Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB

J Agric Food Chem. 2006 Feb 22;54(4):1230-7. doi: 10.1021/jf052359i.

Abstract

In this study, three epigallocatechin gallate glycosides were synthesized by the acceptor reaction of a glucansucrase produced by Leuconostoc mesenteroides B-1299CB with epigallocatechin gallate (EGCG) and sucrose. Each of these glycosides was then purified, and the structures were assigned as follows: epigallocatechin gallate 7-O-alpha-D-glucopyranoside (EGCG-G1); epigallocatechin gallate 4'-O-alpha-D-glucopyranoside (EGCG-G1'); and epigallocatechin gallate 7,4'-O-alpha-D-glucopyranoside (EGCG-G2). One of these compounds (EGCG-G1) was a novel compound. The EGCG glycosides exhibited similar or slower antioxidant effects, depending on their structures (EGCG > or = EGCG-G1 > EGCG-G1' > EGCG-G2), and also manifested a higher degree of browning resistance than was previously noted in EGCG. Also, EGCG-G1, EGCG-G1', and EGCG-G2 were 49, 55, and 114 times as water soluble, respectively, as EGCG.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / pharmacology
  • Catechin / analogs & derivatives*
  • Catechin / biosynthesis
  • Catechin / chemistry
  • Catechin / pharmacology
  • Glycosides / biosynthesis*
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Glycosylation
  • Glycosyltransferases / metabolism*
  • Leuconostoc / enzymology*
  • Molecular Structure
  • Solubility
  • Sucrose / metabolism
  • Water

Substances

  • Antioxidants
  • Glycosides
  • Water
  • Sucrose
  • Catechin
  • epigallocatechin gallate
  • Glycosyltransferases
  • alternansucrase