scholarly journals Enzymatic Synthesis of α-Tocopherol Derivative Glycoside, Daidzein Glycoside, Daidzein Oligosaccharide, Resveratrol Oligosaccharide, and Curcumin Oligosaccharides and Their Anti-Allergic Activity and Neuroprotective Activity

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110290
Author(s):  
Hiroki Hamada ◽  
Hatsuyuki Hamada ◽  
Kohji Ishihara ◽  
Atsuhito Kuboki ◽  
Takafumi Iwaki ◽  
...  
Keyword(s):  
Histamine Release ◽  
Enzymatic Synthesis ◽  
Neuroprotective Activity ◽  
Cyclodextrin Glucanotransferase ◽  
Phytolacca Americana ◽  
Plant Polyphenol

Enzymatic glycosylations of an α-tocopherol derivative, daidzein, resveratrol, and curcumin were investigated. The plant polyphenol, resveratrol, was incubated with glucosyltransferase from Phytolacca americana. The resveratrol glycoside obtained was then incubated with cyclodextrin glucanotransferase to obtain resveratrol oligosaccharide. Daidzein and curcumin were also converted into daidzein glycoside, daidzein oligosaccharide, and curcumin oligosaccharides. Also, α-tocopherol derivative, that is, 2, 5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-ol, was glycosylated. The glycosides and oligosaccharides had strong anti-allergic activity such as suppression of IgE formation, inhibition of histamine release, and inhibition of O2 - generation. In addition, the glycosides and oligosaccharides showed efficient neuroprotective activity by inhibition of phosphodiesterase.

scholarly journals Enzymatic Synthesis and Anti-Allergic Activities of Curcumin Oligosaccharides

2010 ◽  
Vol 3 ◽  
pp. BCI.S2768 ◽  
Author(s):  
Kei Shimoda ◽  
Hiroki Hamada
Keyword(s):  
Mast Cells ◽  
Histamine Release ◽  
Enzymatic Synthesis ◽  
Antibody Formation ◽  
Cyclodextrin Glucanotransferase ◽  
Enzymatic Method ◽  
Inhibitory Effects ◽  
Peritoneal Mast Cells ◽  
Rat Peritoneal Mast Cells ◽  
Suppressive Action

Curcumin 4‘- O-glucooligosaccharides were synthesized by a two step-enzymatic method using almond β-glucosidase and cyclodextrin glucanotransferase (CGTase). Curcumin was glucosylated to curcumin 4‘- O-β-D-glucopyranoside by almond β-glucosidase in 19% yield. Curcumin 4‘- O-β-D-glucopyranoside was converted into curcumin 4‘- O-β-glucooligosaccharides, i.e. 4‘- O-β-maltoside (51%) and 4‘- O-β-maltotrioside (25%), by further CGTase-catalyzed glycosylation. Curcumin 4‘- O-β-glycosides showed suppressive action on IgE antibody formation and inhibitory effects on histamine release from rat peritoneal mast cells.

scholarly journals Synthesis of Resveratrol Glycosides by Plant Glucosyltransferase and Cyclodextrin Glucanotransferase and Their Neuroprotective Activity

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Kei Shimoda ◽  
Naoji Kubota ◽  
Hatsuyuki Hamada ◽  
Hiroki Hamada
Keyword(s):  
Inhibitory Activity ◽  
The Other ◽  
Neuroprotective Activity ◽  
Cyclodextrin Glucanotransferase ◽  
Phytolacca Americana ◽  
Other Hand

Resveratrol was converted by glucosyltransferase from Phytolacca americana into its 3- and 4′- O-β-D-glucosides. On the other hand, further glycosylation of resveratrol 4′- O-β-D-glucoside by cyclodextrin glucanotransferase gave the 4′- O-β-maltoside, 4′- O-β-maltotrioside, 4′- O-β-maltotetraoside, and 4′- O-β-maltopentaoside of resveratrol. The six resveratrol glycosides synthesized here showed higher phosphodiesterase inhibitory activity than resveratrol.

scholarly journals Enzymatic Synthesis of Quercetin Monoglucopyranoside and Maltooligosaccharides

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Ryo Yasukawa ◽  
Natsumi Moriwaki ◽  
Daisuke Uesugi ◽  
Fuya Kaneko ◽  
Hiroki Hamada ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
Cyclodextrin Glucanotransferase ◽  
Phytolacca Americana

Quercetin 3- O-β-monoglucopyranoside and quercetin 3- O-β-maltooligosaccharide were synthesized from quercetin using glucosyltransferase-3 from Phytolacca americana and cyclodextrin glucanotransferase.

scholarly journals Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase

Molecules ◽  
2018 ◽  
Vol 23 (6) ◽  
pp. 1271 ◽  
Author(s):  
José González-Alfonso ◽  
David Rodrigo-Frutos ◽  
Efres Belmonte-Reche ◽  
Pablo Peñalver ◽  
Ana Poveda ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
Cyclodextrin Glucanotransferase

Study on Enzymatic Synthesis of γ-Cyclodextrin with β-Cyclodextrin

2013 ◽  
Vol 774-776 ◽  
pp. 901-906
Author(s):  
Xin Zhi Cao ◽  
Jian Ming You ◽  
Kai Bin Lv
Keyword(s):  
Reaction Time ◽  
Enzymatic Synthesis ◽  
Cyclodextrin Glucanotransferase ◽  
Beta Cyclodextrin ◽  
Gamma Cyclodextrin

Gamma cyclodextrin was produced synthesized from beta cyclodextrin in the presence of glycyrrhizin, using Cyclodextrin glucanotransferase (EC 2.4.1.19) from AlkalophilicBacillus. The results showed that more than 32.7% of beta cyclodextrin substrate was converted to the corresponding gamma cyclodextrin under the following conditions, viz. 200 units enzyme/g of β-CD, 10mmol/L of β-CD concentration, 3% of glycyrrhizin concentration, 27 h of reaction time, 65°C of temperature and a reaction pH of 7.0.

scholarly journals Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Hiroki Hamada ◽  
Hatsuyuki Hamada ◽  
Kei Shimoda
Keyword(s):  
Mast Cells ◽  
Histamine Release ◽  
Inhibitory Activity ◽  
Phytolacca Americana ◽  
Peritoneal Mast Cells ◽  
Rat Peritoneal Mast Cells ◽  
Inhibitory Activities

Glycosylation of (+)-ε-viniferin was investigated using glucosyltransferase from Phytolacca americana ( PaGT3) as a biocatalyst. (+)-ε-Viniferin was converted by PaGT3 into its 4b- and 13b-β-D-glucosides, the inhibitory activities on histamine release from rat peritoneal mast cells of which were higher than that of (+)-ε-viniferin.

scholarly journals Synthesis of Capsaicin Glycosides and 8-Nordihydrocapsaicin Glycosides as Potential Weight-Loss Formulations

2010 ◽  
Vol 3 ◽  
pp. BCI.S2676 ◽  
Author(s):  
Hisashi Katsuragi ◽  
Kei Shimoda ◽  
Eriko Kimura ◽  
Hiroki Hamada
Keyword(s):  
Weight Loss ◽  
Body Weight ◽  
High Fat Diet ◽  
Enzymatic Synthesis ◽  
Cyclodextrin Glucanotransferase ◽  
Inhibitory Effects ◽  
High Fat ◽  
Potential Weight

The enzymatic synthesis of capsaicin glycosides and 8-nordihydrocapsaicin glycosides was investigated using almond β-glucosidase and cyclodextrin glucanotransferase (CGTase). Capsaicin and 8-nordihydrocapsaicin were converted into their β-glucoside and β-maltooligosaccharide (amylose conjugate), i.e. β-maltoside and β-maltotrioside, by sequencial glycosylation with almond β-glucosidase and CGTase. The β-glucoside and β-maltoside of capsaicin and β-glucoside of 8-nordihydrocapsaicin showed inhibitory effects on high-fat-diet-induced elevations in body weight of mice.

Enzymatic synthesis of piceid glycosides by cyclodextrin glucanotransferase

2012 ◽  
Vol 47 (3) ◽  
pp. 528-532 ◽  
Author(s):  
Sindhu Mathew ◽  
Martin Hedström ◽  
Patrick Adlercreutz
Keyword(s):  
Enzymatic Synthesis ◽  
Cyclodextrin Glucanotransferase
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