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

Molecules. 2021 Aug 5;26(16):4746. doi: 10.3390/molecules26164746.

Abstract

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.

Keywords: 3-deoxyglucosone; 5-Hydroxymethylfurfural; LC-MS/MS; black garlic; epigallocatechin gallate.

MeSH terms

  • Catechin / analogs & derivatives*
  • Catechin / pharmacology
  • Deoxyglucose / analogs & derivatives*
  • Deoxyglucose / biosynthesis
  • Deoxyglucose / metabolism
  • Dose-Response Relationship, Drug
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / metabolism
  • Garlic / drug effects*
  • Garlic / metabolism*

Substances

  • 5-hydroxymethylfurfural
  • Catechin
  • Deoxyglucose
  • epigallocatechin gallate
  • Furaldehyde
  • 3-deoxyglucosone