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Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions.
J Agric Food Chem. 2018 Nov 28; 66(47):12536-12543.JA

Abstract

This study aimed to investigate the inhibitory mechanism of epicatechin (EC) on the formation of acrylamide in Maillard reactions. The glucose + asparagine model is a typical chemical system used to investigate acrylamide formation. 5-Hydroxymethylfurfural (HMF) is an important carbonyl intermediate in Maillard reactions and can also react with asparagine to form acrylamide. Time courses showed that EC inhibited more HMF than acrylamide in the glucose + asparagine model heated at 180 °C. The reduction of EC on acrylamide formation in the HMF + asparagine model was about 70%, while that in the glucose + asparagine model was about 50%. Moreover, HMF decreased significantly faster when it was heated in the presence of EC. Liquid chromatography-mass spectrometry analysis revealed the formation of adducts between EC and HMF, and the dimeric adducts were verified in fried potato chips. These results suggested that the condensation of EC and HMF was one of the key steps leading to the inhibition of acrylamide. UV-visible spectra analysis showed that some polymerization products had absorption in the visible region and contributed to the development of browning, which was underestimated in the past.

Authors+Show Affiliations

State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi 214122 , China. School of Food Science and Technology , Jiangnan University , Wuxi 214122 , China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30396275

Citation

Qi, Yajing, et al. "Epicatechin Adducting With 5-Hydroxymethylfurfural as an Inhibitory Mechanism Against Acrylamide Formation in Maillard Reactions." Journal of Agricultural and Food Chemistry, vol. 66, no. 47, 2018, pp. 12536-12543.
Qi Y, Zhang H, Zhang H, et al. Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions. J Agric Food Chem. 2018;66(47):12536-12543.
Qi, Y., Zhang, H., Zhang, H., Wu, G., Wang, L., Qian, H., & Qi, X. (2018). Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions. Journal of Agricultural and Food Chemistry, 66(47), 12536-12543. https://doi.org/10.1021/acs.jafc.8b03952
Qi Y, et al. Epicatechin Adducting With 5-Hydroxymethylfurfural as an Inhibitory Mechanism Against Acrylamide Formation in Maillard Reactions. J Agric Food Chem. 2018 Nov 28;66(47):12536-12543. PubMed PMID: 30396275.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions. AU - Qi,Yajing, AU - Zhang,Hui, AU - Zhang,Hao, AU - Wu,Gangcheng, AU - Wang,Li, AU - Qian,Haifeng, AU - Qi,Xiguang, Y1 - 2018/11/13/ PY - 2018/11/7/pubmed PY - 2018/12/12/medline PY - 2018/11/7/entrez KW - 5-hydroxymethylfurfural (HMF) KW - Maillard reaction KW - acrylamide KW - browning KW - epicatechin (EC) SP - 12536 EP - 12543 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 66 IS - 47 N2 - This study aimed to investigate the inhibitory mechanism of epicatechin (EC) on the formation of acrylamide in Maillard reactions. The glucose + asparagine model is a typical chemical system used to investigate acrylamide formation. 5-Hydroxymethylfurfural (HMF) is an important carbonyl intermediate in Maillard reactions and can also react with asparagine to form acrylamide. Time courses showed that EC inhibited more HMF than acrylamide in the glucose + asparagine model heated at 180 °C. The reduction of EC on acrylamide formation in the HMF + asparagine model was about 70%, while that in the glucose + asparagine model was about 50%. Moreover, HMF decreased significantly faster when it was heated in the presence of EC. Liquid chromatography-mass spectrometry analysis revealed the formation of adducts between EC and HMF, and the dimeric adducts were verified in fried potato chips. These results suggested that the condensation of EC and HMF was one of the key steps leading to the inhibition of acrylamide. UV-visible spectra analysis showed that some polymerization products had absorption in the visible region and contributed to the development of browning, which was underestimated in the past. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/30396275/Epicatechin_Adducting_with_5_Hydroxymethylfurfural_as_an_Inhibitory_Mechanism_against_Acrylamide_Formation_in_Maillard_Reactions_ L2 - https://doi.org/10.1021/acs.jafc.8b03952 DB - PRIME DP - Unbound Medicine ER -