HUANG Caihuan, LI Dan, LONG Chengyan, et al. Mechanism of Acrylamide Elimination by Cysteine and Its Application in Potato Chips[J]. Science and Technology of Food Industry, 2022, 43(22): 287−295. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022010130.
Citation: HUANG Caihuan, LI Dan, LONG Chengyan, et al. Mechanism of Acrylamide Elimination by Cysteine and Its Application in Potato Chips[J]. Science and Technology of Food Industry, 2022, 43(22): 287−295. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022010130.

Mechanism of Acrylamide Elimination by Cysteine and Its Application in Potato Chips

More Information
  • Received Date: January 17, 2022
  • Available Online: September 19, 2022
  • L-cysteine can significantly reduce the content of acrylamide and form new substances. To clarify the reduction mechanism and apply it in potato chip processing, a high purity cysteine-acrylamide adduct was prepared. The target adduct was synthesized by optimizing the reaction conditions, followed by reversed-phase column chromatography for separation and purification. Its structure was identified by mass spectrometry, nuclear magnetic resonance and ultraviolet spectroscopy, and the reduction mechanism was correspondingly elucidated. The cytotoxicity of adducts was evaluated with Caco-2 cell line. Furthermore, potato chips were pretreated with cysteine solutions and the reduction of acrylamide was detected by UPLC-MS. The results showed that the adduct with 95% purity could be obtained when the optimum reaction ratio of cysteine and acrylamide was 1:3 at 120 ℃ for 3 h. Its molecular formula was C6H9NO3S, with relative molecular weight of 192.0641 and maximum UV absorption wavelength of 196 nm. It was formed by Michael addition reaction between the sulfhydryl group of cysteine and the alkenyl group of acrylamide. Compared to acrylamide, the cytotoxicity of the adduct was significantly lower after 24 and 48 h treatment. Potato chips soaked in cysteine solutions of 3 and 5 g/L before frying obtained over 83% of acrylamide reduction rate. In addition, a certain amount of adduct was detected in such potato chips, indicating that cysteine could significantly reduce the acrylamide content in fried potato chips by forming acrylamide adduct.
  • [1]
    RIFAI L, SALEH F A. A review on acrylamide in food: Occurrence, toxicity, and mitigation strategies[J]. International Journal of Toxicology,2020,39(2):93−102. doi: 10.1177/1091581820902405
    [2]
    KUMAR J, DAS S, TEOH S L. Dietary acrylamide and the risks of developing cancer: Facts to ponder[J]. Frontiers in Nutrition,2018,5:14. doi: 10.3389/fnut.2018.00014
    [3]
    HASHEM M M, ABO-EL-SOOUD K, ABD EL-HAKIM Y M, et al. The impact of long-term oral exposure to low doses of acrylamide on the hematological indicators, immune functions, and splenic tissue architecture in rats[J]. International Immunopharmacology,2022,105:108568. doi: 10.1016/j.intimp.2022.108568
    [4]
    MOUSAVI K A, FAKHRI Y, NEMATOLLAHI A, et al. The concentration of acrylamide in different food products: A global systematic review, meta-analysis, and meta-regression[J]. Food Reviews International,2020:1−19.
    [5]
    HIRVONEN T, JESTOI M, TAPANAINEN H, et al. Dietary acrylamide exposure among finnish adults and children: The potential effect of reduction measures[J]. Food Additives & Contaminants: Part A,2011,28(11):1483−1491.
    [6]
    MOLLAKHALILI M N, KHORSHIDIAN N, NEMATOLLAHI A, et al. Acrylamide in bread: A review on formation, health risk assessment, and determination by analytical techniques[J]. Environmental Science and Pollution Research,2021,28(13):15627−15645. doi: 10.1007/s11356-021-12775-3
    [7]
    LIYANAGE D W, YEVTUSHENKO D P, KONSCHUH M, et al. Processing strategies to decrease acrylamide formation, reducing sugars and free asparagine content in potato chips from three commercial cultivars[J]. Food Control,2021,119:107452. doi: 10.1016/j.foodcont.2020.107452
    [8]
    KRISHNAKUMAR T, VISVANATHAN R. Acrylamide in food products: A review[J]. Journal of Food Processing & Technology,2014,5(7):1.
    [9]
    YOSHIOKA T, IZUMI Y, TAKAHASHI M, et al. Identification of acrylamide adducts generated during storage of canned milk coffee[J]. Journal of Agricultural and Food Chemistry,2020,68(12):3859−3867. doi: 10.1021/acs.jafc.9b08139
    [10]
    MUNIR N, ZIA M A, SHARIF S, et al. L-asparaginase potential in acrylamide mitigation from foodstuff: A mini-review[J]. Progress in Nutrition,2019,21(3):498−506.
    [11]
    MILDNER-SZKUDLARZ S, RÓŻAŃSKA M, PIECHOWSKA P, et al. Effects of polyphenols on volatile profile and acrylamide formation in a model wheat bread system[J]. Food Chemistry,2019,297:125008. doi: 10.1016/j.foodchem.2019.125008
    [12]
    KHORSHIDIAN N, YOUSEFI M, SHADNOUSH M, et al. Using probiotics for mitigation of acrylamide in food products: A mini review[J]. Current Opinion in Food Science,2020,32:67−75. doi: 10.1016/j.cofs.2020.01.011
    [13]
    国家卫生和计划生育委员会. 食品安全国家标准 食品添加剂使用标准 GB 2760-2014[S]. 北京: 中国出版社, 2015

    National Health and Family Planning Commission. National standard for food safety: Standard for use of food additives GB 2760-2014[S]. Beijing: China Publishing House, 2015.
    [14]
    汪多仁. 有机食品营养强化剂[M]. 上海: 科技文献出版社, 2008

    WANG D R. Organic food nutritional fortifier[M]. Shanghai: Science and Technology Literature Press, 2008.
    [15]
    ZOU Y, HUANG C, PEI K, et al. Cysteine alone or in combination with glycine simultaneously reduced the contents of acrylamide and hydroxymethylfurfural[J]. LWT-Food Science and Technology,2015,63(1):275−280. doi: 10.1016/j.lwt.2015.03.104
    [16]
    YU M, OU S, LIUMENGZI D, et al. Effect of ten amino acids on elimination of acrylamide in a model reaction system[J]. African Journal of Food Science,2013,7(9):329−333. doi: 10.5897/AJFS2013.1031
    [17]
    JIANG K, HUANG C, JIAO R, et al. Adducts formed during protein digestion decreased the toxicity of five carbonyl compounds against Caco-2 cells[J]. Journal of Hazardous Materials,2019,363:26−33. doi: 10.1016/j.jhazmat.2018.09.053
    [18]
    邹照佳, 郑洁, 黄才欢, 等. 丙烯醛-丙氨酸加合物制备与细胞毒性[J]. 食品科学,2021,42(9):1−6. [ZHOU Z J, ZHENG J, HUANG C H, et al. Preparation and cytotoxicity of acrolein alanine adduct[J]. Food Science,2021,42(9):1−6. doi: 10.7506/spkx1002-6630-20200410-141
    [19]
    HU J, JIANG K, HUANG C, et al. Glycine and serine markedly eliminate methylglyoxal in the presence of formaldehyde via the formation of imidazole salts[J]. Food Chemistry,2022,369:130952. doi: 10.1016/j.foodchem.2021.130952
    [20]
    ZOU Z, YIN Z, OU J, et al. Identification of adducts formed between acrolein and alanine or serine in fried potato crisps and the cytotoxicity-lowering effect of acrolein in three cell lines[J]. Food Chemistry,2021,361:130164. doi: 10.1016/j.foodchem.2021.130164
    [21]
    郭鸿阳, 李瑞阳, 刘启辉, 等. L-半胱氨酸对油炸薯片中有害醛、AGEs的抑制作用及其品质的改善效果[J]. 食品科学,2022,43(4):60−68. [GUO H Y, LI R Y, LIU Q H, et al. Inhibitory effect of L-cysteine on harmful aldehydes and AGEs in fried potato chips and its quality improvement[J]. Food Science,2022,43(4):60−68.
    [22]
    刘刚, 王毅, 王鑫, 等. 液相色谱串联质谱法测定加工食品中丙烯酰胺的含量[J]. 西华大学学报(自然科学版),2021,40(2):97−102. [LIU G, WANG Y, WANG X, et al. Determination of acrylamide in processed food by liquid chromatography tandem mass spectrometry[J]. Journal of Xihua University (Natural Science Edition),2021,40(2):97−102. doi: 10.12198/j.issn.1673-159X.3399
    [23]
    KOBAYASHI A, GOMIKAWA S, YAMAZAKI A, et al. Elimination of acrylamide by moderate heat treatment below 120 ℃ with lysine and cysteine[J]. Food Science and Technology Research,2014,20(5):979−985. doi: 10.3136/fstr.20.979
    [24]
    OU J, ZHENG J, HUANG J, et al. Interaction of acrylamide, acrolein, and 5-hydroxymethylfurfural with amino acids and DNA[J]. Journal of Agricultural and Food Chemistry,2020,68(18):5039−5048. doi: 10.1021/acs.jafc.0c01345
    [25]
    LIM H H, SHIN H S. A new derivatization approach with d-cysteine for the sensitive and simple analysis of acrylamide in foods by liquid chromatography-tandem mass spectrometry[J]. Journal of Chromatography A,2014,1361:117−124. doi: 10.1016/j.chroma.2014.07.094
    [26]
    SCHWEND T, SCHABACKER J, WETTERAUER B, et al. Uptake of S-(3-amino-3-oxopropyl)-cysteine by Caco-2 cells[J]. Zeitschrift für Naturforschung C,2008,63(11-12):913−918.
    [27]
    ZAMORA R, DELGADO R M, HIDALGO F J. Model reactions of acrylamide with selected amino compounds[J]. Journal of Agricultural and Food Chemistry,2010,58(3):1708−1713. doi: 10.1021/jf903378x
    [28]
    ADAMS A, HAMDANI S, LANCKER F V, et al. Stability of acrylamide in model systems and its reactivity with selected nucleophiles[J]. Food Research International,2010,43(5):1517−1522. doi: 10.1016/j.foodres.2010.04.033
    [29]
    BENT G A, MARAGH P, DASGUPTA T, et al. Kinetic and density functional theory (DFT) studies of in vitro reactions of acrylamide with the thiols: Captopril, l-cysteine, and glutathione[J]. Toxicology Research,2015,4(1):121−131. doi: 10.1039/C4TX00070F
  • Cited by

    Periodical cited type(0)

    Other cited types(3)

Catalog

    Article Metrics

    Article views (337) PDF downloads (13) Cited by(3)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return