Synthesis, Structure Analyses, and Characterization of Novel Epigallocatechin Gallate (EGCG) Glycosides Using the Glucansucrase from Leuconostoc mesenteroides B-1299CB

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 follo...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2006-02, Vol.54 (4), p.1230-1237
Main Authors: Moon, Young-Hwan, Lee, Jin-Ha, Ahn, Joon-Seob, Nam, Seung-Hee, Oh, Deok-Kun, Park, Don-Hee, Chung, Hyun-Ju, Kang, Seongsoo, Day, Donal F, Kim, Doman
Format: Article
Language:English
Subjects:
antioxidant activity
Antioxidants - pharmacology
Biological and medical sciences
Catechin - analogs & derivatives
Catechin - biosynthesis
Catechin - chemistry
Catechin - pharmacology
chemical structure
enzyme activity
epigallocatechin gallate
epigallocatechin gallate glycosides
flavanols
Food industries
Fundamental and applied biological sciences. Psychology
glucansucrase
glycosides
Glycosides - biosynthesis
Glycosides - chemistry
Glycosides - pharmacology
Glycosylation
Glycosyltransferases - metabolism
hexosyltransferases
Leuconostoc - enzymology
Leuconostoc mesenteroides
Molecular Structure
Solubility
sucrose
Sucrose - metabolism
Water
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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-α-d-glucopyranoside (EGCG-G1); epigallocatechin gallate 4‘-O-α-d-glucopyranoside (EGCG-G1‘); and epigallocatechin gallate 7,4‘-O-α-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 ≥ 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. Keywords: Leuconostoc mesenteroides glucansucrase; EGCG; glycoside; acceptor reaction
ISSN:0021-8561
1520-5118
DOI:10.1021/jf052359i