Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB.
Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl beta-isomaltoside (arbutin-G1), 4-hydroxyphenyl beta-isomaltotrioside (arbutin-G2), according to the results of (1)H, (13)C, heteronuclear single-quantum coherence, (1)H-(1)H COSY, and heteronuclear multiple-bond correlation analyses. Arbutin glucoside (4-hydroxyphenyl beta-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin.
Moon
Young Hwan
YH
School of Biological Sciences and Technology, The Research Institute for Catalysis and Institute of Bioindustrial Technology, Chonnam National University, Gwangju, 500-757, South Korea.
Nam
Seung Hee
SH
Kang
Jin
J
Kim
Young-Min
YM
Lee
Jin-Ha
JH
Kang
Hee-Kyung
HK
Breton
Vincent
V
Jun
Woo-Jin
WJ
Park
Ki-Deok
KD
Kimura
Atsuo
A
Kim
Doman
D
D001104:Arbutin / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D005960:Glucosides / Q000302:isolation & purification / Q000378:metabolism*; D016695:Glycosyltransferases / Q000378:metabolism*; D007934:Leuconostoc / Q000201:enzymology* / Q000378:metabolism
D005960:Glucosides; D001104:Arbutin; D016695:Glycosyltransferases; C033837:alternansucrase