Synthesis and Characterization of 6-O-Acyl-2-O-α-D-glucopyranosyl-L-ascorbic Acids with a Branched-acyl Chain
スポンサーリンク
概要
- 論文の詳細を見る
We previously reported the chemical synthesis of a series of novel monoacylated vitamin C derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) possessing a straight-acyl chain of varying length from C_4 to C_18, as effective skin antioxidants. In this paper, we describe branched type of 6-Acyl-AA-2G derivatives (6-bAcyl-AA-2G) synthesized by use of a 2-branched-chain fatty acid anhydride as an acyl donor. The stability of 6-bAcyl-AA-2G in neutral solution was much higher than that of 6-Acyl-AA-2G, while they were susceptible to enzymatic hydrolysis for exerting vitamin C effect. These branched derivatives as well as 6-Acyl-AA-2G increased the radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl and the lipophilicity in octanol/water-partitioning systems with increasing length of their acyl group. In addition, the 6-bAcyl-AA-2G derivative with an acyl chain of C_12, 6-bDode-AA-2G had the excellent solubility to various solvents, suggesting easy handling in cosmetic use. These characteristics of 6-bAcyl-AA-2G may be available for skin care application as an effective antioxidant.
- 公益社団法人日本薬学会の論文
- 2003-02-01
著者
-
SASAKI Kenji
Department of Chemical Science and Engineering, Kobe University
-
Yamamoto Itaru
岡山大学 薬学部免疫医薬品化学
-
YAMAMOTO Itaru
Department of Radiology, Kanazawa Medical University
-
Kawasaki Daisuke
Department of Second Cardiology, National Hospital Organazation Kagoshima Medical Center
-
Yamamoto I
Okayama Univ. Okayama Jpn
-
TAI Akihiro
Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University
-
GOHDA Eiichi
Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University
-
Kawasaki Daisuke
Department Of Immunochemistry Faculty Of Pharmaceutical Sciences Okayama University
-
Kawasaki Daisuke
Department Of Biology School Of Education Waseda University
-
Yamamoto Itaru
Department Of Immunochemistry Faculty Of Pharmaceutical Science Okayama University
-
Tai A
Department Of Immunochemistry Faculty Of Pharmaceutical Sciences Okayama University
-
Tai Akihiro
Department Of Immunochemistry Division Of Pharmaceutical Sciences Okayama University Graduate School
-
Gohda Eiichi
Dep. Of Immunochemistry Div. Of Pharmaceutical Sciences Okayama Univ. Graduate School Of Medicine De
-
Gohda E
Department Of Immunochemistry Faculty Of Pharmaceutical Sciences Okayama University
-
Gohda Eiichi
Department Of Immunochemistry Division Of Pharmaceutical Sciences Okayama University Graduate School
-
Sasaki Kenji
Department Of Bioindustrial Informatics And Genomics Graduate School Of Agricultural Science Tohoku
-
Sasaki Kenji
Department Of Pharmaceutical Fundamental Science Faculty Of Pharmaceutical Sciences Okayama Universi
-
Yamamoto I
Department Of Immunochemistry Division Of Pharmaceutical Sciences Okayama University Graduate School
-
GOHDA Eiichi
Department of Biochemistry, Faculty of Dentistry, Osaka University
関連論文
- Mixing Characteristics in a Conical Taylor-Couette Flow System at Low Reynolds Numbers
- Weak Hyperon-Nucleon Interaction in a Quark Model and Application to the pn → Λp Scattering
- EFFECT OF MODEST PERIOPERATIVE INTAKE OF IMMUNO-NUTRITION RICH IN ω -3 POLYUNSATURATED FATTY ACIDS ON IL-10 IN ESOPHAGEAL CANCER PATIENTS
- Cervical Approach for Resection of a Pedunculated Giant Atypical Lipomatous Tumor of the Esophagus
- Laparoscopic Long Esophagomyotomy with Dor's Fundoplication Using a Transhiatal Approach for an Epiphrenic Esophageal Diverticulum
- Value of whole-body FDG PET in management of lung cancer
- Changes in regional cerebral blood flow in irradiated regions and normal brain after stereotactic radiosurgery
- Single photon emission CT images in a case of intraventricular neurocytoma
- Medical vs Surgical Treatment of Acute Aortic Dissection in an Intensive Care Unit : 54th Annual Scientific Session of the Japanese Circulation Society
- Long-term prophylactic effects of intravesical instillation of thiotepa and oral administration of UFT on the recurrence of superficial bladder cancer after transurethral resection
- PJ-641 Sleep Apnea Increases Left Ventricular End Systolic Volume(LVESV) and Worsens Renal Function in Patients with Ischemic Heart Disease(Chronic coronary heart disease / Remodeling(03)(IHD),Poster Session(Japanese),The 72nd Annual Scientific Meeting of
- PJ-571 Umcomprehensible BNP Levels in Patients with Mechanical Prosthesis in Mitral Position Presenting Congestive Heart Failure (CHF)(Valvular heart disease/Pericarditis/Cardiac tumor(04)(M),Poster Session(Japanese),The 72nd Annual Scientific Meeting of
- OJ-241 Oxygen Desaturation Index (ODI) Can be Adverse Predictor for Remote Cardiac Function in Patients with AML undergone Early Revascularization(Chronic coronary heart disease/Remodeling-1, The 71st Annual Scientific Meeting of the Japanese Circulation
- Antiscorbutic Activity of L-Ascorbic Acid 2-Glucoside and Its Availability as a Vitamin C Supplement in Normal Rats and Guinea Pigs
- Formation of a Stable Ascorbic Acid 2-Glucoside by Specific Transglucosylation with Rice Seed α-Glucosidase(Biological Chemistry)
- ACTIVATION OF MURINE LYMPHOCYTES BY 2-MERCAPTOETHANOL AND RELATED THIOL COMPOUNDS AND ITS MECHANISM. II. EFFECT OF THIOL COMPOUNDS ON THE VIABILITY OF THE LYMPHOCYTES UNDER A CYSTINE-DEFICIENT CULTURE CONDITION
- IN VITRO GENERATION OF ANTIGEN-SPECIFIC SUPPRESSOR T CELL ACTIVITY. CULTURE CONDITIONS FOR ABROGATING THE INDUCTION OF NONSPECIFIC SUPPRESSOR T CELLS
- Behavior of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in a Flour-water Suspension and Its Effectiveness as a Dough Improver
- CT and MRI Findings of Xanthoma in the Orbitofrontal Region
- An isocratic HPLC method for the simultaneous determination of novel stable lipophilic ascorbic acid derivatives and their metabolites
- Characterization of the Radical-Scavenging Reaction of 2-O-Substituted Ascorbic Acid Derivatives, AA-2G, AA-2P, and AA-2S : A Kinetic and Stoichiometric Study(Biopharmacy)
- Inhibition of Hepatocyte Growth Factor Induction in Human Dermal Fibroblasts by Tryptanthrin(Pharmacology)
- pH-Dependent Long-term Radical Scavenging Activity of AA-2G and 6-Octa-AA-2G against 2,2 '-Azinobis(3-ethylbenzothiazoline-6-sulfonic acid) Radical Cation(Biopharmacy)
- Long-Term Radical Scavenging Activity of AA-2G and 6-Acyl-AA-2G against 1,1-Diphenyl-2-picrylhydrazyl
- Ascorbic Acid 2-O-α-Glucoside-Induced Redox Modulation in Human Keratinocyte Cell Line, SCC : Mechanisms of Photoprotective Effect against Ultraviolet Light B
- Ascorbic Acid 2-O-α-Glucoside, a Stable Form of Ascorbic Acid, Rescues Human Keratinocyte Cell Line, SCC, from Cytotoxicity of Ultraviolet Light B
- Purification and Characterization of a Mouse Hepatocyte Growth-Stimulating Factor from the Liver of Carbon Tetrachloride-Treated Mice
- A Simple Model for Hydrogen Re-distribution in Zirconium-lined Fuel Claddings
- Heterologous Expression of Aspergillus oryzae Xylose Reductase and Xylitol Dehydrogenase Genes Facilitated Xylose Utilization in the Yeast Saccharomyces cerevisiae
- Inhibition of Hepatocyte Growth Factor Production in Human Fibroblasts by Ursodeoxycholic Acid(Pharmacology)
- Biological and Immunological Properties of Human Hepatocyte Growth Factor from Plasma of Patients with Fulminant Hepatic Failure.
- Vitamin C Activity in Guinea Pigs of 6-O-Acyl-2-O-α-D-glucopyranosyI-L-ascorbic Acids with a Branched-acyl Chain(Food & Nutrition Science)
- Synthesis and Characterization of 6-O-Acyl-2-O-α-D-glucopyranosyl-L-ascorbic Acids with a Branched-acyl Chain
- Bioavailability of a Series of Novel Acylated Ascorbic Acid Derivatives, 6-O-Acyl-2-O-α-D-glucopyranosyl-L-ascorbic Acids, as an Ascorbic Acid Supplement in Rats and Guinea Pigs(Food & Nutrition Sience)
- Radical Scavenging Activity against 1, 1-Diphenyl-2-picrylhydrazyl of Ascorbic Acid 2-Glucoside(AA-2G)and 6-Acyl-AA-2G
- Ecabet sodium prevents the delay of wound repair in intestinal epithelial cells induced by hydrogen peroxide
- Novel Evidence Suggesting Clostridium difficile Is Present in Human Gut Microbiota More Frequently than Previously Suspected
- Development of a rapid semi-quantitative immunochromatographic assay for serum hepatocyte growth factor and its usefulness in acute liver failure
- Enhancement of Immunoglobulin M Production in B Cells by the Extract of Red Bell Pepper
- THE USE OF β-CYCLODEXTRIN IN LYMPHOCYTE CULTURE. INDUCTION OF THE PRIMARY ANTIBODY RESPONSE IN VITRO IN CALF SERUM- OR NEWBORN BOVINE SERUM-CONTAINING CULTURE MEDIUM
- Cloning of the Genes for the Pituitary Glycoprotein Hormone α and Follicle-Stimulating Hormone β Subunits in the Japanese Crested Ibis, Nipponia nippon(Endocrinology)
- Cloning of the Gene for the Thyrotropin β Subunit in the Japanese Crested Ibis, Nipponia nippon(Endocrinology)
- ENZYME IMMUNOASSAY OF CYCLIC NUCLEOTIDE
- Activation of Murine Peritoneal Macrophages by Water-Soluble Extracts of Bursaphelenchus xylophilus, a Pine Wood Nematode
- Augmentation by Bursaphelenchus xylophilus, a Pine Wood Nematode, of Polyclonal IgE Production Induced by Lipopolysaccharide Plus Interleukin-4 in Murine Splenocytes
- Gallium-67-citrate scintigraphy of primary renal lymphoma
- Enhancing Effect of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid, a Stable Ascorbic Acid Derivative, on Collagen Synthesis
- Augmentation of Antigen-Specific Antibody Production and IL-10 Generation with a Fraction from Rooibos (Aspalathus linearis) Tea
- DEGRADATION OF HISTAMINE IN THE PRESENCE OF ASCORBIC ACID AND Cu^ ION : INVOLVEMENT OF HYDROGEN PEROXIDE
- Requirement of Cytokines for Augmentation of the Antigen-Specific Antibody Responses by Ascorbate in Cultured Murine T-Cell-Depleted Splenocytes
- Enhancement of Neurite Outgrowth in PC12 Cells Stimulated with Cyclic AMP and NGF by 6-Acylated Ascorbic Acid 2-O-α-Glucosides(6-Acyl-AA-2G),Novel Lipophilic Ascorbate Derivatives
- Synthesis of 2-O-α-D-Glucopyranosyl L-Ascorbic Acid by Cyclomaltodextrin Glucanotransferase from Bacillus stearothermophilus(Biological Chemistry)
- Effects of Rooibos Tea Extract on Antigen-specific Antibody Production and Cytokine Generation in Vitro and in Vivo(Biochemistry & Molecular Biology)
- DEVELOPMENT OF ENZYME IMMUNOASSAY FOR MABUTEROL AND ITS APPLICATION FOR METABOLIC STUDY
- An Increase in Histone Acetylation and IL-2 Antagonizing the Immunoinhibitory Effect Are Necessary for Augmentation by Butyrate of in Vitro Anti-TNP Antibody Production
- In Vitro Augmentation of Natural Killer Activity and Interferon-γ Production in Murine Spleen Cells with Agaricus blazei Fruiting Body Fractions
- Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Pyridine
- Sucralfate prevents the delay of wound repair in intestinal epithelial cells by hydrogen peroxide through NF-κB pathway
- Comparison of Capsular Morphology between two Different Surface Structures of Silicone Implants
- ACTIVATION OF ALLOPURINOL OXIDIZING ENZYME ACTIVITY OF THE DIALYSATE OF MOUSE LIVER SUPERNATANT BY MONOVALENT CATIONS
- 2-O-α-D-Glucopyranosyl-L-ascorbic Acid Scavenges 1,1-Diphenyl-2-picrylhydrazyl Radicals via a Covalent Adduct Formation
- Determination of ascorbic acid and its related compounds in foods and beverages by hydrophilic interaction liquid chromatography
- EFFECT OF N-(2-CARBOXYPHENYL)-4-CHLOROANTHRANILIC ACID DISODIUM SALT (CCA) ON THE INDUCTION OF HELPER AND SUPPRESSOR T CELLS IN VITRO AND IN VIVO
- ANTIGEN-INDUCED ELEVATION OF CYCLIC GMP LEVEL IN PLASMA AND ITS ABOLITION IN EXPERIMENTALLY IMMUNOSUPPRESSIVE MICE
- TISSUE DISTRIBUTION AND CHARACTERISTICS OF XANTHINE OXIDASE AND ALLOPURINOL OXIDIZING ENZYME
- 2-O-α-D-Glucopyranosyl-L-ascorbic Acid Scavenges 1,1-Diphenyl-2-picrylhydrazyl Radicals via a Covalent Adduct Formation
- Rapid Progression of Aortic Regurgitation with Thoracic Aortic Aneurysm due to Takayasu Arteritis Associated with Ulcerative Colitis
- Heterologous Expression of Aspergillus oryzae Xylose Reductase and Xylitol Dehydrogenase Genes Facilitated Xylose Utilization in the Yeast Saccharomyces cerevisiae
- Histone Hyperacetylation Plays a Role in Augmentation of IL-4-Induced IgE Production in LPS-Stimulated Murine B-Lymphocytes by Sodium Butyrate
- HDI-13 ACTIVE HEAD SLIDERS USING PIEZOELECTRIC THIN FILMS FOR FLYING-HEIGHT CONTROL
- Successful Management of a Giant Arteriovenous Fistula with a Combination of Selective Embolization and Excision : Report of a Case
- Augmentation of Antigen-Specific Antibody Production and IL-10 Generation with a Fraction from Rooibos (Aspalathus linearis) Tea
- Design of a Wearable Micro Info-Broadcasting System(Poster Session 6 (uT Technology))
- DEVELOPMENT OF A MOTORCYCLE SIMULATOR USING PARALLEL MANIPULATOR AND HEAD MOUNTED DISPLAY
- Glucagon Degradation in Fraction of Big Plasma Glucagon in Rats Treated with Carbon Tetrachloride
- In Vitro and In Vivo Prolonged Biological Activities of Novel Vitamin C Derivative, 2-O-α-D-Glucopyranosyl-L-Ascorbic Acid (AA-2G), in Cosmetic Fields
- Hyperinsulinemia induces hypertension associated with neurogenic vascular dysfunction resulting from abnormal perivascular innervations in rat mesenteric resistance arteries
- Augmentation of the antibody response by lipoic acid in mice. I. Analysis of the mode of action in an in vitro culture system.
- Restriction of Mast Cell Proliferation through Hyaluronan Synthesis by Co-cultured Fibroblasts
- Abnormality of the delayed type hypersensitivity (DTH) response to Bordetella pertussis in spontaneously hypertensive rats (SHR).
- An experimental model of nephritis induced by calf serum injection in mice.
- In Situ Intestinal Absorption of 2-0-.ALPHA.-D-Glucopyranosyl-L-Ascorbic Acid in Guinea Pigs.
- Vitamin C Activity of 2-O-.ALPHA.-D-Glucopyranosyl-L-Ascorbic Acid in Guinea Pigs.
- Alendronate Modulates Osteogenesis of Human Osteoblastic Cells In Vitro.
- Induction of prolonged elevation of interleukin 2 in the culture medium of murine splenocytes by their precultivation before mitogenic stimulations and its potentiation by glucocorticoid treatment and restraint stress loading.
- Immunomodulatory activity of the newly synthesized compound TOK-8801 (N-(2-phenylethyl)-3,6,6-trimethyl-5,6-dihydroimidazo(2,1-b)thiazole-2-carboxamide).
- The use of .BETA.-cyclodextrin-containing culture medium for in vitro evaluation of immunomodulating agents.
- Augmentation of in vitro antibody response by disulfide compounds. I. Comparison between intermolecular and intramolecular disulfides.
- Altered expression of angiogenic factors in the VEGF-Ets-1 cascades in inflammatory bowel disease
- Butyrate Enhances the In Vitro Anti-SRBC (Sheep Red Blood Cell) Antibody Responses in Murine Splenocytes.
- Inhibition of proliferative responses and interleukin 2 productions by salazosulfapyridine and its metabolites.
- Enhancement by Ascorbic Acid 2-Glucoside or Repeated Additions of Ascorbate of Mitogen-Induced IgM and IgG Productions by Human Peripheral Blood Lymphocytes.
- Augmentation of the antibody response by lipoic acid in mice. II Restoration of the antibody response in immunosuppressed mice.