Structure-reactivity relationships of flavan-3-ols on product generation in aqueous glucose/glycine model systems

Yuko Noda, Devin G Peterson

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

Ring structure-reactivity relationships of three flavan-3-ols [epicatechin (EC), epicatechin gallate (ECG), and epigallocatechin gallate (EGCG)] and three simple phenolic compounds (1,3,5-trihydroxybenzene, 1,2,3-trihydroxybenzene, and methylgallate as the analogous individual A, B, and C benzene rings of EGCG) on product generation in an aqueous glucose-glycine reaction model system (125°C and 30 min) were investigated. The addition of EC, ECG, or EGCG to a glucose-glycine model was reported to similarly significantly reduce the formation of pyrazine, methyl-substituted pyrazines, and cyclotene. All three flavan-3-ols were also reported to generate phenolic-C2, C 3, C4, and C6 sugar fragment adducts and to statistically reduce the concentration of glyoxal, glycolaldehyde, methylglyoxal, hydroxyacetone, diacetyl, acetoin, and 3-deoxyglucosone during the reaction time course, except for the EGCG reaction where 3-deoxyglucosone was not statistically different from the control after 20 min. For the simple phenolic compounds, methylgallate followed by 1,2,3-trihydroxybenzene was the least reactive, while 1,3,5-trihydroxybenzene was reported as the most reactive phenolic structure for quenching or reducing the concentration of the α-hydroxy-and α-dicarbonyl sugar fragments during the reaction time course. These results imply that the main mechanism flavan-3-ols reduced product generation was phenolic-sugar fragment carbonyl trapping reactions primarily on the A ring (the meta-polyhydroxylated benzene ring) or not due to the alteration of the reaction reduction potential.

Original languageEnglish (US)
Pages (from-to)3686-3691
Number of pages6
JournalJournal of agricultural and food chemistry
Volume55
Issue number9
DOIs
StatePublished - May 2 2007

Keywords

  • Aroma generation
  • Carbonyl reactions
  • Flavan-3-ols
  • Maillard reaction
  • Polyhydroxybenzene
  • Structure-reactivity
  • Sugar fragments
  • Trapping

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