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 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.
Department of Material and Chemical and Biochemical Engineering, Engineering Research Institute, Chonnam National University, Gwangju 500-757, South Korea.
Young-Hwan
YH
Moon
Jin-Ha
JH
Lee
Joon-Seob
JS
Ahn
Seung-Hee
SH
Nam
Deok-Kun
DK
Oh
Don-Hee
DH
Park
Hyun-Ju
HJ
Chung
Seongsoo
S
Kang
Donal F
DF
Day
Doman
D
Kim
D000975:Antioxidants / Q000494:pharmacology; D002392:Catechin / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000096:biosynthesis* / Q000737:chemistry* / Q000494:pharmacology; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism*; D007934:Leuconostoc / Q000201:enzymology*; D015394:Molecular Structure; D012995:Solubility; D013395:Sucrose / Q000378:metabolism; D014867:Water
D000975:Antioxidants; D006027:Glycosides; D014867:Water; D013395:Sucrose; D002392:Catechin; C045651:epigallocatechin gallate; D016695:Glycosyltransferases; C033837:alternansucrase