Journal of Agricultural and Food Chemistry
Article
(15) Torres, P.; Poveda, A.; Jimenez-Barbero, J.; Parra, J. L.; Comelles,
F.; Ballesteros, A. O.; Plou, F. J. Enzymatic synthesis of α-glucosides of
resveratrol with surfactant activity. Adv. Synth. Catal. 2011, 353, 1077−
1086.
(16) Bungaruang, L.; Gutmann, A.; Nidetzky, B. Leloir glycosyl-
transferases and natural product glycosylation: biocatalytic synthesis of
the C-glucoside nothofagin, a major antioxidant of redbush herbal tea.
Adv. Synth. Catal. 2013, 355, 2757−2763.
(17) Yamamoto, I.; Muto, N.; Nagata, E.; Nakamura, T.; Suzuki, Y.
Formation of a stable L-ascorbic acid α-glucoside by mammalian α-
glucosidase-catalyzed transglucosylation. Biochim. Biophys. Acta, Gen.
Subj. 1990, 1035, 44−50.
(18) Plaza, M.; Pozzo, T.; Liu, J.; Ara, K. Z. G.; Turner, C.; Karlsson, E.
N. Substituent effects on in vitro antioxidizing properties, stability, and
solubility in flavonoids. J. Agric. Food Chem. 2014, 62, 3321−3333.
(19) Hollman, P. C. H.; Bijsman, M.; van Gameren, Y.; Cnossen, E. P.
J.; de Vries, J. H. M.; Katan, M. B. The sugar moiety is a major
determinant of the absorption of dietary flavonoid glycosides in man.
Free Radical Res. 1999, 31, 569−573.
(20) Zhu, X.; Schmidt, R. R. New principles for glycoside-bond
formation. Angew. Chem., Int. Ed. 2009, 48, 1900−1934.
(21) Muthana, S.; Cao, H. Z.; Chen, X. Curr. Opin. Chem. Biol. 2009,
13, 573−581.
(22) de Roode, B. M.; Franssen, M. C. R.; Van der Padt, A.; Boom, R.
M. Perspectives for the industrial enzymatic production of glycosides.
Biotechnol. Prog. 2003, 19, 1391−1402.
(23) Palcic, M. M. Glycosyltransferases as biocatalysts. Curr. Opin.
Chem. Biol. 2011, 15, 226−233.
(24) Desmet, T.; Soetaert, W. Enzymatic glycosyl transfer:
mechanisms and applications. Biocatal. Biotransform. 2011, 29, 1−18.
(25) Desmet, T.; Soetaert, W. Broadening the synthetic potential of
disaccharide phosphorylases through enzyme engineering. Process
Biochem. 2012, 47, 11−17.
(26) Kitao, S.; Sekine, H. α-D-Glucosyl transfer to phenolic compounds
by sucrose phosphorylase from Leuconostoc mesenteroides and
production of α-arbutin. Biosci., Biotechnol., Biochem. 1994, 58, 38−42.
(27) De Winter, K.; Verlinden, K.; Kren, V.; Weignerova, L.; Soetaert,
W.; Desmet, T. Ionic liquids as cosolvents for glycosylation by sucrose
phosphorylase: balancing acceptor solubility and enzyme stability. Green
Chem. 2013, 15, 1949−1955.
(28) De Winter, K.; Desmet, T.; Devlamynck, T.; Van Renterghem, L.;
Verhaeghe, T.; Pelantova, H.; Kren, V.; Soetaert, W. Biphasic catalysis
with disaccharide phosphorylases: chemoenzymatic synthesis of α-D-
glucosides using sucrose phosphorylase. Org. Process Res. Dev. 2014, 18,
781−787.
(29) Giang Hai, T.; Desmet, T.; De Groeve, M. R. M.; Soetaert, W.
Probing the active site of cellodextrin phosphorylase from Clostridium
stercorarium: kinetic characterization, ligand docking, and site-directed
mutagenesis. Biotechnol. Prog. 2011, 27, 326−332.
phosphorylase from Clostridium thermocellum. Biochimie 2010, 92,
1818−1826.
(35) Reichenbecher, M.; Lottspeich, F.; Bronnenmeier, K. Purification
and properties of a cellobiose phosphorylase (CepA) and a cellodextrin
phosphorylase (CepB) from the cellulolytic thermophile Clostridium
stercorarium. Eur. J. Biochem. 1997, 247, 262−267.
(36) Samain, E.; Lancelonpin, C.; Ferigo, F.; Moreau, V.; Chanzy, H.;
Heyraud, A.; Driguez, H. Phosphorolytic synthesis of cellodextrins.
Carbohydr. Res. 1995, 271, 217−226.
(37) Rothwell, J. A.; Day, A. J.; Morgan, M. R. A. Experimental
determination of octanol-water partition coefficients of quercetin and
related flavonoids. J. Agric. Food Chem. 2005, 53, 4355−4360.
(38) Moon, Y. H.; Lee, J. H.; Ahn, J. S.; Nam, S. H.; Oh, D. K.; Park, D.
H.; Chung, H. J.; Kang, S.; Day, D. F.; Kim, D. Synthesis, structure
analyses, and characterization of novel epigallocatechin gallate (EGCG)
glycosides using the glucansucrase from Leuconostoc mesenteroides B-
1299CB. J. Agric. Food Chem. 2006, 54, 1230−1237.
(39) Kaminaga, Y.; Nagatsu, A.; Akiyama, T.; Sugimoto, N.; Yamazaki,
T.; Maitani, T.; Mizukami, H. Production of unnatural glucosides of
curcumin with drastically enhanced water solubility by cell suspension
cultures of Catharanthus roseus. FEBS Lett. 2003, 555, 311−316.
(40) Noguchi, A.; Inohara-Ochiai, M.; Ishibashi, N.; Fukami, H.;
Nakayama, T.; Nakao, M. A novel glucosylation enzyme: molecular
cloning, expression, and characterization of Trichoderma viride
JCM22452 α-amylase and enzymatic synthesis of some flavonoid
monoglucosides and oligoglucosides. J. Agric. Food Chem. 2008, 56,
12016−12024.
(41) Zielinska, D.; Wiczkowski, W.; Piskula, M. K. Determination of
the relative contribution of quercetin and its glucosides to the
antioxidant capacity of onion by cyclic voltammetry and spectrophoto-
metric methods. J. Agric. Food Chem. 2008, 56, 3524−3531.
(42) Takebayashi, J.; Ishii, R.; Chen, J.; Matsumoto, T.; Ishimi, Y.; Tai,
A. Reassessment of antioxidant activity of arbutin: multifaceted
evaluation using five antioxidant assay systems. Free Radical Res. 2010,
44, 473−478.
(43) Xie, J.; Schaich, K. M. Re-evaluation of the 2,2-diphenyl-1-
picrylhydrazyl free radical (DPPH) assay for antioxidant activity. J. Agric.
Food Chem. 2014, 62, 4251−4260.
(44) Makris, D. P.; Rossiter, J. T. Domestic processing of onion bulbs
(Allium cepa) and asparagus spears (Asparagus officinalis): effect on
flavonol content and antioxidant status. J. Agric. Food Chem. 2001, 49,
3216−3222.
(45) Valentova, K.; Vrba, J.; Bancirova, M.; Ulrichova, J.; Kren, V.
Isoquercitrin: pharmacology, toxicology, and metabolism. Food Chem.
Toxicol. 2014, 68, 267−282.
(46) Xiao, J.; Hoegger, P. Stability of dietary polyphenols under the cell
culture conditions: avoiding erroneous conclusions. J. Agric. Food Chem.
2015, 63, 1547−1557.
(30) De Winter, K.; Van Renterghem, L.; Wuyts, K.; Pelantova, H.;
Kren, V.; Soetaert, W.; Desmet, T. Chemoenzymatic synthesis of β-D-
glucosides using cellobiose phosphorylase from Clostridium thermocel-
lum. Adv. Synth. Catal. 2015, 357, 1961−1969.
(31) Dirks-Hofmeister, M. E.; Verhaeghe, T.; De Winter, K.; Desmet,
T. Creating space for large acceptors: rational biocatalyst design for
resveratrol glycosylation in an aqueous system. Angew. Chem., Int. Ed.
2015, 54, 9289−9292.
(32) De Winter, K.; Soetaert, W.; Desmet, T. An imprinted cross-
linked enzyme aggregate (iCLEA) of sucrose phosphorylase: combining
improved stability with altered specificity. Int. J. Mol. Sci. 2012, 13,
11333−11342.
(33) Gawronski, J. D.; Benson, D. R. Microtiter assay for glutamine
synthetase biosynthetic activity using inorganic phosphate detection.
Anal. Biochem. 2004, 327, 114−118.
(34) Nakai, H.; Hachem, M. A.; Petersen, B. O.; Westphal, Y.;
Mannerstedt, K.; Baumann, M. J.; Dilokpimol, A.; Schols, H. A.; Duus, J.
O.; Svensson, B. Efficient chemoenzymatic oligosaccharide synthesis by
reverse phosphorolysis using cellobiose phosphorylase and cellodextrin
I
J. Agric. Food Chem. XXXX, XXX, XXX−XXX