title: Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties.
abstract: Novel ampelopsin glucosides (AMPLS-Gs) were enzymatically synthesized and purified using a Sephadex LH-20 column. Each structure of the purified AMPLS-Gs was determined by nuclear magnetic resonance, and the ionic product of AMPLS-G1 was observed at m/z 505 (C₂₁H₂₂O₁₃·Na)⁺ using matrix-assisted laser desorption ionization time-of-flight mass spectrometry. AMPLS-G1 was identified as ampelopsin-4'-O-α-D-glucopyranoside. The optimum condition for AMPLS-G1, determined using response surface methodology, was 70 mM ampelopsin, 150 mM sucrose, and 1 U/mL dextransucrase, which resulted in an AMPLS-G1 yield of 34 g/L. The purified AMPLS-G1 displayed 89-fold increased water solubility and 14.5-fold browning resistance compared to those of AMPLS and competitive inhibition against tyrosinase with a K(i) value of 40.16 μM. This value was smaller than that of AMPLS (K(i)=62.56 μM) and much smaller than that of β-arbutin (K(i)=514.84 μM), a commercial active ingredient of whitening cosmetics. These results indicate the potential of AMPLS and AMPLS-G1 as superior ingredients for functional cosmetics.
authors.affiliation: Department of Biotechnology and Bioengineering and Research Institute for Catalysis, Chonnam National University, Gwang-Ju 500-757, Republic of Korea.
authors.forename: Hye-Jin
authors.initials: HJ
authors.lastname: Woo
authors.forename: Hee-Kyoung
authors.initials: HK
authors.lastname: Kang
authors.forename: Thi Thanh Hanh
authors.initials: TT
authors.lastname: Nguyen
authors.forename: Go-Eun
authors.initials: GE
authors.lastname: Kim
authors.forename: Young-Min
authors.initials: YM
authors.lastname: Kim
authors.forename: Jun-Seong
authors.initials: JS
authors.lastname: Park
authors.forename: Duwoon
authors.initials: D
authors.lastname: Kim
authors.forename: Jaeho
authors.initials: J
authors.lastname: Cha
authors.forename: Young-Hwan
authors.initials: YH
authors.lastname: Moon
authors.forename: Seung-Hee
authors.initials: SH
authors.lastname: Nam
authors.forename: Yong-mei
authors.initials: YM
authors.lastname: Xia
authors.forename: Atsuo
authors.initials: A
authors.lastname: Kimura
authors.forename: Doman
authors.initials: D
authors.lastname: Kim
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D001426:Bacterial Proteins / Q000378:metabolism*; D001709:Biotechnology; D055598:Chemical Phenomena; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D005419:Flavonoids / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D005960:Glucosides / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D005964:Glucosyltransferases / Q000378:metabolism*; D006031:Glycosylation; D007934:Leuconostoc / Q000201:enzymology*; D015416:Maillard Reaction; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D012995:Solubility; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000975:Antioxidants; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D005419:Flavonoids; D005960:Glucosides; C106407:ampelopsin; D014442:Monophenol Monooxygenase; D005964:Glucosyltransferases; C020025:dextransucrase