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Chlorogenic acid increased acrylamide formation through promotion of HMF formation and 3-aminopropionamide deamination.
J Hazard Mater. 2014 Mar 15; 268:1-5.JH

Abstract

This research was aimed to investigate why chlorogenic acid, presents at high concentrations in some food raw material, influences acrylamide formation. In the asparagine/glucose Maillard reaction system (pH=6.8), addition of chlorogenic acid significantly increased acrylamide formation and inhibited its elimination. In contrast, the quinone derivative of chlorogenic acid decreased acrylamide formation. Three mechanisms may be involved for increasing acrylamide formation by chlorogenic acid. Firstly, it increased the formation of HMF, which acts as a more efficient precursor than glucose to form acrylamide. Secondly, it decreased activation energy for conversion of 3-aminopropionamide (3-APA) to acrylamide (from 173.2 to 136.6kJ/mol), and enhances deamination from 3-APA. And thirdly, it prevented attack of the produced acrylamide from free radicals by keeping high redox potential during the Maillard reaction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China. Electronic address: tosy@jnu.edu.cn.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China.

Department of Chemistry, Jinan University, Guangzhou 510632, China.

MeSH

AcrylamideChlorogenic AcidDeaminationFlavonesFood ContaminationMaillard ReactionModels, ChemicalOxidation-ReductionQuinonesbeta-Alanine

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24462985

Citation

Cai, Yun, et al. "Chlorogenic Acid Increased Acrylamide Formation Through Promotion of HMF Formation and 3-aminopropionamide Deamination." Journal of Hazardous Materials, vol. 268, 2014, pp. 1-5.

Cai Y, Zhang Z, Jiang S, et al. Chlorogenic acid increased acrylamide formation through promotion of HMF formation and 3-aminopropionamide deamination. J Hazard Mater. 2014;268:1-5.

Cai, Y., Zhang, Z., Jiang, S., Yu, M., Huang, C., Qiu, R., Zou, Y., Zhang, Q., Ou, S., Zhou, H., Wang, Y., Bai, W., & Li, Y. (2014). Chlorogenic acid increased acrylamide formation through promotion of HMF formation and 3-aminopropionamide deamination. Journal of Hazardous Materials, 268, 1-5. https://doi.org/10.1016/j.jhazmat.2013.12.067

Cai Y, et al. Chlorogenic Acid Increased Acrylamide Formation Through Promotion of HMF Formation and 3-aminopropionamide Deamination. J Hazard Mater. 2014 Mar 15;268:1-5. PubMed PMID: 24462985.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Chlorogenic acid increased acrylamide formation through promotion of HMF formation and 3-aminopropionamide deamination. AU - Cai,Yun, AU - Zhang,Zhenhua, AU - Jiang,Shanshan, AU - Yu,Miao, AU - Huang,Caihuan, AU - Qiu,Ruixia, AU - Zou,Yueyu, AU - Zhang,Qirui, AU - Ou,Shiyi, AU - Zhou,Hua, AU - Wang,Yong, AU - Bai,Weibing, AU - Li,Yiqun, Y1 - 2014/01/07/ PY - 2013/10/18/received PY - 2013/12/29/revised PY - 2013/12/30/accepted PY - 2014/1/28/entrez PY - 2014/1/28/pubmed PY - 2014/10/21/medline KW - 3-Aminopropionamide KW - Acrylamide KW - Chlorogenic acid KW - HMF SP - 1 EP - 5 JF - Journal of hazardous materials JO - J Hazard Mater VL - 268 N2 - This research was aimed to investigate why chlorogenic acid, presents at high concentrations in some food raw material, influences acrylamide formation. In the asparagine/glucose Maillard reaction system (pH=6.8), addition of chlorogenic acid significantly increased acrylamide formation and inhibited its elimination. In contrast, the quinone derivative of chlorogenic acid decreased acrylamide formation. Three mechanisms may be involved for increasing acrylamide formation by chlorogenic acid. Firstly, it increased the formation of HMF, which acts as a more efficient precursor than glucose to form acrylamide. Secondly, it decreased activation energy for conversion of 3-aminopropionamide (3-APA) to acrylamide (from 173.2 to 136.6kJ/mol), and enhances deamination from 3-APA. And thirdly, it prevented attack of the produced acrylamide from free radicals by keeping high redox potential during the Maillard reaction. SN - 1873-3336 UR - https://www.unboundmedicine.com/medline/citation/24462985/Chlorogenic_acid_increased_acrylamide_formation_through_promotion_of_HMF_formation_and_3_aminopropionamide_deamination_ DB - PRIME DP - Unbound Medicine ER -