Reduction of 3-Deoxyglucosone by Epigallocatechin Gallate Results Partially from an Addition Reaction: The Possible Mechanism of Decreased 5-Hydroxymethylfurfural in Epigallocatechin Gallate-Treated Black Garlic

An-Ting Tu; Jer-An Lin; Chieh-Hsiu Lee; Yi-An Chen; Jung-Tsung Wu; Ming-Shiun Tsai; Kuan-Chen Cheng; Chang-Wei Hsieh

doi:10.3390/molecules26164746

Molecules (Aug 2021)

Reduction of 3-Deoxyglucosone by Epigallocatechin Gallate Results Partially from an Addition Reaction: The Possible Mechanism of Decreased 5-Hydroxymethylfurfural in Epigallocatechin Gallate-Treated Black Garlic

An-Ting Tu,
Jer-An Lin,
Chieh-Hsiu Lee,
Yi-An Chen,
Jung-Tsung Wu,
Ming-Shiun Tsai,
Kuan-Chen Cheng,
Chang-Wei Hsieh

Affiliations

An-Ting Tu: Department of Food Science and Biotechnology, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung 402, Taiwan
Jer-An Lin: Graduate Institute of Food Safety, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung 402, Taiwan
Chieh-Hsiu Lee: Department of Food Science and Biotechnology, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung 402, Taiwan
Yi-An Chen: College of Biotechnology and Bioresources, Da-Yeh University, 168 University Rd., Dacun, Chang-Hua 515, Taiwan
Jung-Tsung Wu: College of Biotechnology and Bioresources, Da-Yeh University, 168 University Rd., Dacun, Chang-Hua 515, Taiwan
Ming-Shiun Tsai: Department of Food Science and Biotechnology, Da-Yeh University, 168 University Rd., Dacun, Chang-Hua 515, Taiwan
Kuan-Chen Cheng: Graduate Institute of Food Science and Technology, National Taiwan University, 1, Sec 4, Roosevelt Rd., Taipei 106, Taiwan
Chang-Wei Hsieh: Department of Food Science and Biotechnology, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung 402, Taiwan

DOI: https://doi.org/10.3390/molecules26164746
Journal volume & issue: Vol. 26, no. 16
p. 4746

Abstract

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5-Hydroxymethylfurfural (5-HMF) is a harmful substance generated during the processing of black garlic. Our previous research demonstrated that impregnation of black garlic with epigallocatechin gallate (EGCG) could reduce the formation of 5-HMF. However, there is still a lack of relevant research on the mechanism and structural identification of EGCG inhibiting the production of 5-HMF. In this study, an intermediate product of 5-HMF, 3-deoxyglucosone (3-DG), was found to be decreased in black garlic during the aging process, and impregnation with EGCG for 24 h further reduced the formation of 3-DG by approximately 60% in black garlic compared with that in the untreated control. The aging-mimicking reaction system of 3-DG + EGCG was employed to determine whether the reduction of 3-DG was the underlying mechanism of decreased 5-HMF formation in EGCG-treated black garlic. The results showed that EGCG accelerated the decrease of 3-DG and further attenuated 5-HMF formation, which may be caused by an additional reaction with 3-DG, as evidenced by LC-MS/MS analysis. In conclusion, this study provides new insights regarding the role of EGCG in blocking 5-HMF formation.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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