Syntheses of α-Arbutin-α-Glycosides and Their Inhibitory Effects on Human Tyrosinase(Enzymology, Protein Engineering, and Enzyme Technology)
スポンサーリンク
概要
- 論文の詳細を見る
α-Arbutin is a tyrosinase inhibitor. We synthesized α-arbutin-α-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase from Bacillus macerans using α-arbutin and starch as acceptor and donor molecules, respectively. We isolated and characterized two major products from the reaction mixture. The structural analyses using ^<13>C- and ^1H-NMR spectroscopy proved that they were 4-hydroxyphenyl α-maltoside (α-Ab-α-G1) and 4-hydroxyphenyl α-maltotrioside (α-Ab-α-G2). Both α-Ab-α-G1 and α-Ab-α-G2 exhibited competitive-type inhibition on human tyrosinase as α-arbutin does. Their K_i values were calculated to be 0.6 mM and 2.8 mM, respectively, which is slightly and significantly higher than that of α-arbutin (0.2 mM).
- 社団法人日本生物工学会の論文
- 2005-03-25
著者
-
SUGIMOTO Kazuhisa
Biochemical Research Laboratory, Ezaki Glico Co., Ltd.
-
NISHIMURA Takahisa
Biochemical Research Laboratory, Ezaki Glico Co., Ltd.
-
KURIKI Takashi
Biochemical Research Laboratory, Ezaki Glico Co., Ltd.
-
TO-O Kenji
Health Science Laboratory, Ezaki Glico
-
NOMURA Koji
Biochemical Research Laboratory, Ezaki Glico
-
Kuriki T
Health Science Laboratory Ezaki Glico
-
Nomura K
Biochemical Research Laboratory Ezaki Glico
-
Kometani T
Biochemical Res. Lab. Ezaki Glico Co. Ltd.
-
Kuriki T
Ezaki Glico Co. Ltd. Osaka Jpn
-
KISO TARO
Osaka Municipal Technical Research Institute
-
SUGIMOTO KENJI
Laboratory of Applied Molecular Biology, Division of Applied Biochemistry, Graduate School of Agricu
-
To-o Kenji
Health Science Laboratory Ezaki Glico
-
Kuriki Takashi
Biochemical Research Laboratory Ezaki Glico
-
Kuriki Takashi
Biochemical Research Laboratories Ezaki Glico Co. Ltd.
-
Sugimoto Kazuhisa
Biochemical Research Laboratory Ezaki Glico
-
Sugimoto Kazuhisa
Department Of Applied Biological Chemistry College Of Agriculture University Of Osaka Prefecture
-
Nishimura Takahisa
Biochemical Research Laboratory Ezaki Glico Co. Ltd.
-
Nishimura Takahisa
Research Planning Division Ezaki Glico
-
Nishimura Takahisa
Department Of Agricultural Chemistry College Of Agriculture University Of Osaka Prefecture
-
Sugimoto Kenji
江崎グリコ生物化学研究所
-
Nishimura T
Central Research Laboratories Kissei Pharmaceutical Co. Ltd.
-
Nomura Koji
Biochemical Research Laboratory Ezaki Glico
-
Kuriki T
Biochemical Research Laboratory Ezaki Glico
-
Sugimoto Kenji
Laboratory Of Applied Molecular Biology Division Of Applied Biochemistry Graduate School Of Agricult
-
Nomura K
Institute Of Agriculture And Forestry University Of Tsukuba
-
Sugimoto Kenji
Laboratory Of Applied Molecular Biology Department Of Applied Biochemistry Osaka Prefecture Universi
関連論文
- α-アルブチンの開発 : 工業スケールでの製造および美白化粧品原料への応用
- Experimental study on cross-reactivity of α-arbutin toward p-phenylenediamine and hydroquinone in guinea pigs
- Regioselective Hydrolytic Cleavage of N-Terminal Myristoyl-peptide
- Highly Branched Oligosaccharides Produced by the Transglycosylation Reaction of Neopullulanase
- Neopullulanase Exhibits Distinct Specificity toward Amylose and Amylopectin
- Substrate Specificity of Glycyrrhizinic Acid Hydrolase(Organic Chemistry)
- Synthesis of 3,4-Dimethoxyphenyl β-D-Glucopyranoside and Its Related Glycosides by Cultured Plant Cells
- Glucosylation of Capsaicin by Cell Suspension Cultures of Coffea arabica
- Glucosylation of Vanillin by Cultured Plant Cells
- A New Method for Precipitation of Various Glucosides with Cyclodextrin Glucano-transferase
- Sweetness of Glycyrrhetic Acid 3-O-β-D-Monoglucuronide and the Related Glycosides
- 馬鈴薯澱粉由来リン酸化オリゴ糖の生産と応用
- Novel Transglucosylating Reaction of Sucrose Phosphorylase to Carboxylic Compounds Such as Benzoic Acid(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Syntheses of α-Arbutin-α-Glycosides and Their Inhibitory Effects on Human Tyrosinase(Enzymology, Protein Engineering, and Enzyme Technology)
- Inhibitory Effects of α-Arbutin on Melanin Synthesis in Cultured Human Melanoma Cells and a Three-Dimensional Human Skin Model (Pharmacology)
- Absorbability of Calcium from Calcium-bound Phosphoryl Oligosaccharides in Comparison with That from Various Calcium Compounds in the Rat Ligated Jejunum Loop(Food & Nutrition Science)
- Syntheses of Arbutin-α-glycosides and a Comparison of Their Inhibitory Effects with Those of α-Arbutin and Arbutin on Human Tyrosinase
- Substrate Selectivity in Aspergillus niger KU-8 Acid Phosphatase II Using Phosphoryl Oligosaccharides
- A Novel Acid Phosphatase from Aspergillus niger KU-8 That Specifically Hydrolyzes C-6 Phosphate Groups of Phosphoryl Oligosaccharides
- Effect of Phosphoryl Oligosaccharides on Iron Solubility under Neutral Conditions
- Studies of Phosphoryl Oligosaccharides Prepared from Potato Starch〔含 質疑応答〕 (糖質関連酵素化学シンポジウム)
- The Structures of Phosphoryl Oligosaccharides Prepared from Potato Starch
- Regioselective Cleavage of Myristoyl-Peptide in Acidic Solution
- Inhibition of β-Fructofuranosidases and α-Glucosidases by Synthetic Thio-fructofuranoside(Biochemistry & Molecular Biology)
- Alteration of the Specificity of Neopullulanase by Protein Engineering (アミラ-ゼシンポジウム(1991)特集)
- Synthesis of Glycosyl Glycerol by Cyclodextrin Glucanotransferases(ENZYMOLOGY,PROTEIN ENGINEERING,AND ENZYME TECHNOLOGY)
- Hydrolysis of β-Glucosyl Ester Linkage of p-Hydroxybenzoyl β-D-Glucose, a Chemically Synthesized Glucoside, by β-Glucosidases
- Hydrolysis of β-Galactosyl Ester Linkage by β-Galactosidases
- Transfructosylation of Thiol Group by β-Fructofuranosidases
- Galactosylation of Thiol Group by β-Galactosidase
- Purification and Some Properties of a β-Glucosidase from Flavobacterium johnsonae
- Purification and Characterization of a Novel β-Glucosidase from Clavibacter michiganense That Hydrolyzes Glucosyl Ester Linkage in Steviol Glycosides
- Evaluation of Chiral Amino Acid Discrimination by a Permethylated Cyclic Tetrasaccharide, cyclo-{→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→}, Using FAB Mass Spectrometry
- Asymmetric Borane Reduction of Prochiral Ketone Using Chiral Bis(α,α-diphenyl-2-pyrrolidinemethanol) Carbonate
- The Practical Synthesis of a Uterine Relaxant, Bis(2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl}amino)-1, 2, 3, 4-tetrahydronaphthalen-7-yl]oxy}-N, N-dimethylacetamide)Sulfate(KUR-1246)
- The Practical Synthesis of(2S)-7-Methoxy-1, 2, 3, 4-tetrahydro-2-naphthylamine via Optical Resolution of 2-(3-Methoxybenzyl)succinic Acid
- Asymmetric Borane Reduction of Prochiral Ketones Using Aluminum Triethoxide and Chiral Amino Alcohls
- Synthesis of Anacardic Acids, 6-[8(Z), 11(Z)-Pentadecadienyl]salicylic Acid and 6-[8(Z), 11(Z), 14-Pentadecatrienyl]salicylic Acid
- Improved Synthesis of Anacardic Acids, 6-Pentadecylsalicylic Acid and 6-[8(Z)-Pentadecenyl]salicylic Acid, from Aldehyde and Acetoacetate
- Optimization of Operating Conditions in a High-Shear Mixer Using DEM Model : Determination of Optimal Fill Level
- DEM Simulation of Mixing and Segregation in High-Shear Mixer (特集 材料設計のための粉体評価)
- Effect of B-Ions Substitution in [(K_Bi_)-(Na_Bi_)](Ti-B)O_3 System with B=Zr, Fe_Nb_, Zn_Nb_ or Mg_Nb_
- B-Ion Substitution in (Pb-A)(Ti-B)O_3 Systems with A=Na_Bi_ or K_Bi_ and B=Zr, Fe_Nb_, Zn_Nb_, Mg_Nb_ or Mg_W_
- Piezoelectricity and Electrostriction in Ferroelectric Actuators
- Isolation and Characterization of Matrix Associated Region DNA Fragments in Rice (Oryza sativa L.)
- Nuclear Matrix and Matrix AssociationRegion DNA in Rice (Oryza sativa L.)
- Centromere/Kinetochore Localization of Human Centromere Protein A (CENP-A) Exogenously Expressed as a Fusion to Green Fluorescent Protein
- Functional Domain Structure of Human Heterochromatin Protein HP1^ : Involvement of Internal DNA-Binding and C-Terminal Self-Association Domains in the Formation of Discrete Dots in Interphase Nuclei
- Human Homolog of Drosophila Heterochromatin-Associated Protein 1 (HP1) Is a DNA-Binding Protein Which Possesses a DNA-Binding Motif with Weak Similarity to That of Human Centromere Protein C(CENP-C)
- Characterization of Dimers of Hydroquinone Glucosides Produced by Peroxidase-Catalyzed Polymerization
- Purification and Characterization of a Carbohydrate:Acceptor Oxidoreductase from Paraconiothyrium sp. That Produces Lactobionic Acid Efficiently
- Purification and Characterization of a Novel α-Glucuronidase from Aspergillus niger Specific for O-α-D-Glucosyluronic Acid α-D-Glucosiduronic Acid
- Molecular Dynamics of Aurora-A Kinase in Living Mitotic Cells Simultaneously Visualized with Histone H3 and Nuclear Membrane Protein Importinα
- A Sports Drink Based on Highly Branched Cyclic Dextrin Generates Few Gastrointestinal Disorders in Untrained Men during Bicycle Exercise
- Antidiabetic Effect of Glycyrrhizin Genetically Diabetic KK-A^y Mice
- Enhancement of Swimming Endurance in Mice by Highly Branched Cyclic Dextrin
- cDNA Cloning of the Cry1Aa Receptor Variants from Bombyx mori and Their Expression in Mammalian Cells
- Rhythmic Cycle of Clathrin-Coated Pit Formation at the trans-Golgi Network in Human MDA-MB-435 Cells
- Purification and Some Properties of a Levanase from Streptomyces sp. No. 7-3(Biological Chemistry)
- Effect of Glycolipid Fraction on Fat Bloom in Dark and Milk Chocolates
- Preparation of Glyceroglycolipids from Pumpkin and Their Effects on Polymorphic Transformation of Cocoa Butter
- A Method for Preparation of Soluble Carthamin, Red Pigment from Safflower, Using Glycosyl Hesperidin
- Effects of Salt and pH on Property of Emulsion Prepared with Monolaurin Monoglucoside
- Synthesis of Monoacylglycerol Monoglucoside by Rice α-Glucosidase and Its Foaming Power
- Lowering Effect of Phenolic Glycosides on the Rise in Postprandial Glucose in Mice
- Glucosylation of Acetic Acid by Sucrose Phosphorylase
- Structures and Activity of Cellulase Inhibitors Enzymatically Synthesized from Cello-oligosaccharides and 1-Deoxynojirimycin
- Effects of Glyceroglycolipids Prepared from Various Natural Materials on Polymorphic Transformation of Cocoa Butter
- Acceptor Specificity of Cyclodextrin Glucanotransferase from an Alkalophilic Bacillus Species and Synthesis of Glucosyl Rhamnose
- Synthesis of Neohesperidin Glycosides and Naringin Glycosides by Cyclodextrin Glucanotransferase from an Alkalophilic Bacillus Species
- Cyclic α-1,4-Glucan Formation by Bacterial α-Amylases
- New Proteinacens α-Amylase inhibitor (T-76) from Streptomyces nitrosporeus
- 工業用酵素への異種機能導入へのアプローチ
- Glucosylation of Caffeic Acid with Bacillus subtilis X-23 α-Amylase and a Description of the Glucosides
- Transglycosylation to Hesperidin by Cyclodextrin Glucanotransferase from an Alkalophilic Bacillus Species in Alkaline pH and Properties of Hesperidin Glycosides
- Acceptor Specificity in the Glucosylation Reaction of Bacillus subtilis X-23 α-Amylase towards Various Phenolic Compounds and the Structure of Kojic Acid Glucoside
- Purification and Some Properties of α-Amylase from Bacillus subtilis X-23 That Glucosylates Phenolic Compounds Such as Hydroquinone
- Puritication and Characterization of Cyclodextrin Glucanotransferase from an Alkalophilic Bacillus Species and Transglycosylation at Alkaline pHs
- Visualization of Aberrant Perinuclear Microtubule Aster Organization by Microtubule-Destabilizing Agents
- Dynamic Behavior of FCHO1 Revealed by Live-Cell Imaging Microscopy : Its Possible Involvement in Clathrin-Coated Vesicle Formation
- Rhythmic Cycle of Clathrin-Coated Pit Formation at the trans-Golgi Network in Human MDA-MB-435 Cells
- Glucosylation of Acetic Acid by Sucrose Phosphorylase
- The Concept of the α-Amylase Family : Structural Similarity and Common Catalytic Mechanism
- Prevention of Hesperidin Crystal Formation in Canned Mandarin Orange Syrup and Clarified Orange Juice by Hesperidin Glycosides
- Characterization of Dimers of Hydroquinone Glucosides Produced by Peroxidase-Catalyzed Polymerization
- An Antigenic Determinant on Human Centromere Protein B (CENP-B) Available for Production of Human-Specific Anticentromere Antibodies in Mouse
- Purification and Some Properties of a New Levanase from Bacillus sp. No. 71
- Purification and Characterization of a Carbohydrate : Acceptor Oxidoreductase from Paraconiothyrium sp. That Produces Lactobionic Acid Efficiently
- Casein Kinase II Site of Human Centromere Protein B (CENP-B) is Phosphorylated in Vitro
- Function of Second Glucan Binding Site Including Tyrosines 54 and 101 in Thermus aquaticus Amylomaltase(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Improvement of a Venus-Based Bimolecular Fluorescence Complementation Assay to Visualize bFos-bJun Interaction in Living Cells
- α-アミラーゼファミリーの概念 : 糖質酵素のタンパク質工学のための合理的手段
- 緒言 : 糖質科学と糖質工学の産業的利用
- Molecular Behavior in Living Mitotic Cells of Human Centromere Heterochromatin Protein HP1α Ectopically Expressed as a Fusion to Red Fluorescent Protein
- Improvement of a Venus-Based Bimolecular Fluorescence Complementation Assay to Visualize bFos-bJun Interaction in Living Cells
- A Rapid and Simple Method of Evaluating the Dimeric Tendency of Fluorescent Proteins in Living Cells Using a Truncated Protein of Importin α as Fusion Tag
- Optimization of Lactobionic Acid Production by Acetobacter orientalis Isolated from Caucasian Fermented Milk, "Caspian Sea Yogurt"
- Neopullulanase Exhibits Distinct Specificity toward Amylose and Amylopectin
- Effects of Salts and pH on the Emulsion Stabilities of Digalactosylmonoacylglycerol and Trigalactosylmonoacylglycerol.
- Foaming Power and Emulsifying Properties of the Hydrolyzates by Lipase from Rhizopus arrhizus on Digalactosyldiacylglycerol and Trigalactosyldiacylglycerol Extracted from Pumpkin.