title: Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB.
abstract: 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.
authors.affiliation: School of Biological Sciences and Technology, The Research Institute for Catalysis and Institute of Bioindustrial Technology, Chonnam National University, Gwangju, 500-757, South Korea.
authors.forename: Young Hwan
authors.initials: YH
authors.lastname: Moon
authors.forename: Seung Hee
authors.initials: SH
authors.lastname: Nam
authors.forename: Jin
authors.initials: J
authors.lastname: Kang
authors.forename: Young-Min
authors.initials: YM
authors.lastname: Kim
authors.forename: Jin-Ha
authors.initials: JH
authors.lastname: Lee
authors.forename: Hee-Kyung
authors.initials: HK
authors.lastname: Kang
authors.forename: Vincent
authors.initials: V
authors.lastname: Breton
authors.forename: Woo-Jin
authors.initials: WJ
authors.lastname: Jun
authors.forename: Ki-Deok
authors.initials: KD
authors.lastname: Park
authors.forename: Atsuo
authors.initials: A
authors.lastname: Kimura
authors.forename: Doman
authors.initials: D
authors.lastname: Kim
mesh_terms: 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
chemical_list: D005960:Glucosides; D001104:Arbutin; D016695:Glycosyltransferases; C033837:alternansucrase