Saponin and Sapogenol. XXIII. Degradation of Methyl Glucuronide and Methyl Galacturonide by Lead Tetraacetate Oxidation followed by Alkali Treatment
スポンサーリンク
概要
- 論文の詳細を見る
In a continuing study on the selective cleavage method for the β-D-glucuronide linkage contained in oligoglycoside, the behavior of methyl β-D- and α-D-glucuronides and methyl β-D- and α-D-galacturonides has been examined towards lead tetraacetate oxidation followed by alkali treatment. It has been found that the lead tetraacetate degradation method is a useful tool for cleavage of the α-D-glucuronide and β-D-galacturonide linkages as well as the β-D-glucuronide linkage. The α-D-galacturonide has been found to show considerable resistance for lead tetraacetate oxidation. In addition, the dialdehyde intermediate (23) in the reaction sequence has been shown to be a promissing species which is readily convertible to nitrocyclitols.
- 公益社団法人日本薬学会の論文
- 1978-02-25
著者
-
吉川 雅之
Faculty of Pharmaceutical Sciences, Osaka University
-
北川 勲
Faculty Of Pharmaceutical Sciences Osaka University
-
門田 明子
Faculty Of Pharmaceutical Sciences Osaka University:(present Address)department Of Chemistry School
関連論文
- Structures of Echinoside A and B, Two Antifungal Oligoglycosides from the Sea Cucumber Actinopyga echinites (JAEGER)
- Marine Natural Products. XXIV. : The Absolute Stereostructure of Misakinolide A, a Potent Cytotoxic Dimeric Macrolide from an Okinawan Marine Sponge Theonella sp.
- Marine Natural Products. XXIII. : Three New Cytotoxic Dimeric Macrolides, Swinholides B and C and Isoswinholide A, Congeners of Swinholide A, from the Okinawan Marine Sponge Theonella swinhoei
- Marine Natural Products. XXII. : The Absolute Stereostructure of Swinholide A, a Potent Cytotoxic Dimeric Macrolide from the Okinawan Marine Sponge Theonella swinhoei
- STRUCTURE OF THEONELLAPEPTOLIDE ID, A NEW BIOACTIVE PEPTOLIDE FROM AN OKIKAWAN MARINE SPONGE, THEONELLA SP. (THEONELLIAE)
- Chemical Transformation of Terpenoids. X. Ionophoretic Activities of Macrocyclic Lactone Epoxides Synthesized from Geraniol
- Chemical Transformation of Terpenoids. IX. Ionophoretic Activities of Macrocyclic Lactone Epoxides Synthesized from E, E-Farnesol
- Syntheses of a Glycerophospholipid, C16-Platelet Activating Factor and a Palmitoyl Analogue of M-5,an Anti-inflammatory Glyceroglycolipid
- Syntheses of Two Pairs of Enantiomeric C18-Sphingosines and a Palmitoyl Analogue of Gaucher Spleen Glucocerebroside
- Marine Natural Products. XXXII. Absolute Configurations of C-4 of the Manoalide Family, Biologically Active Sesterterpenes from the Marine Sponge Hyrtions erecta
- Marine Natural Products. XXXI. Structure-Activity Correlation of a Potent Cytotoxic Dimeric Macrolide Swinholide A, from the Okinawan Marine Sponge Theonella swinhoei, and Its Isomers
- ALTOHYRTINS B AND C AND 5-DESACETYLALTOHYRTIN A, POTENT CYTOTOXIC MACROLIDE CONGENERS OF ALTOHYRTIN A, FROM THE OKINAWAN MARINE SPONGE HYRTIOS ALTUM
- Indonesian Medicinal Plants. XI. Chemical Structures of Caesaldekarins a and b, Two New Cassane-Type Furanoditerpenes from the Roots of Caesalpinia major (Fabaceae)
- A NEW METHOD FOR MEASURING IONOPHORETIC ACTIVITY USING A GLASS-CELL APPARATUS EQUIPPED WITH ARTIFICIAL MEMBRANES
- ESCINS-Ia, Ib, IIa, IIb, AND IIIa, BIOACTIVE TRITERPENE OLIGOGLYCOSIDES FROM THE SEEDS OF AESCULUS HIPPOCASTANUM L. : THEIR INHIBITORY EFFECTS ON ETHANOL ABSORPTION AND HYPOGLYCEMIC ACTIVITY ON GLUCOSE TOLERANCE TEST
- Chemical Studies of Chinese Licorice-Roots. I. Elucidation of Five New Flavonoid Constituents from the Roots of Glycyrrhiza glabra L. Collected in Xinjiang
- ABSOLUTE STEREOSTRUCTURES OF PAEONISOTHUJONE, A NOVEL SKELETAL MONOTERPENE KETONE, AND DEOXYPAEONISUFFRONE, AND ISOPAEONISUFFRAL, TWO NEW MONOTERPENES, FROM MOUTAN CORTEX
- ABSOLUTE STEREOSTRUCTURES OF PAEONISUFFRONE AND PAEONISUFFRAL, TWO NEW LABILE MONOTERPENES, FROM CHINESE MOUTAN CORTEX
- Histochemistry. VI. Tocopherols and Isoflavones in Soybeans (Glycine max MERRILL, Seeds)
- Histochemistry. V. Soyasaponins in Soybeans (Glycine max MERRILL, Seeds)
- Indonesian Medicinal Plants. X. Chemical Structures of Four New Triterpene-Glycosides, Gongganosides D, E, F, and G, and Two Secoiridoid-Glucosides from the Bark of Bhesa paniculata (Celastraceae)
- Indonesian Medicinal Plants. IX. Chemical Structures of Gongganosides A, B, and C, Three New Quinovic Acid Glycosides from the Bark of Bhesa paniculata (Celastraceae)
- Marine Natural Products. XXX. Two New 3-Keto-4-methylene Steroids, Theonellasterone and Conicasterone, and a Diels-Alder Type Dimeric Steroid Bistheonellasterone, from the Okinawan Marine Sponge Theonella swinhoei
- Marine Natural Products. XXIX. Heterosigma-glycolipids I, II, III, and IV, Four Diacylglyceroglycolipids Possessing ω3-Polyunsaturated Fatty Acid Residues, from the Raphidopycean Dinoflagellate Heterosigma akashiwo
- ARAGUSPONGINES B, C, D, E, F, G, H, AND J, NEW VASODILATIVE BIS-1-OXAQUINOLIZIDINE ALKALOIDS FROM AN OKINAWAN MARINE SPONGE, XESTOSPONGIA SP.
- Chemical Transformation of Terpenoids. VI. Syntheses of Chiral Segments, Key Building-Blocks for the Left Half of Taxane-Type Diterpenoids
- Chemical Transformation of Terpenoids. IV. Acid Treatment of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1,2,2-trimethylcyclopentane Derivatives : Ring Enlargement Reactions and Successive Migrations of Methyl Residues
- Chemical Transformation of Terpenoids. III. Syntheses of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1,2,2-trimethylcyclopentane Derivatives from d-Camphor via 5-Oxo-d-bornyl Acetate
- Chemical Transformation of Terpenoids. II. Acid Treatment of (3S)-1-Vinyl-, (3S)-1-Hydroxypropenyl-, and (3S)-1-Epoxyethyl-1,2,2-trimethylcyclopentane Derivatives : Ring Enlargement Reactions and Successive Migrations of Methyl Residues
- Chemical Transformation of Terpenoids. I. Syntheses of (3S)-1-Vinyl-, (3S)-1-Hydroxypropenyl-, and (3S)-1-Epoxyethyl-1,2,2-trimethylcyclopentane Derivatives from d-Camphor via d-Camphoric Acid
- Biogenetically Patterned Transformation of Eudesmanolide to Eremophilanolide. V. Studies on Stereochemical Factors for Favorable Conversion of 5α, 6α-Epoxy-eudesman-8β, 12-olide leading to Eremophilane-type Derivatives
- On the Constituents of Picrorhiza kurrooa. (1). The Structure of Picroside I, a Bitter Principle of the Subterranean Part
- Saponin and Sapogenol. IV. Seeds Sapogenols of Aesculus turbinata BLUME. On the Configuration of Hydroxyl Functions in Ring E of Aescigenin, Protoaescigenin, and Isoaescigenin in Relation to Barringtogenol C and Theasapogenol A
- Saponin and Sapogenol. III. Seeds Sapogenols of Thea sinensis L. (3). Theasapogenol E and Minor Sapogenols
- Saponin and Sapogenol. II. Seeds Sapogenols of Thea sinensis L. (2). Theasapogenol A
- Saponin and Sapogenol. I. Seeds Sapogenols of Thea sinensis L. (1). Barringtogenol C (=Theasapogenol B)
- Comparative Study on the Sapogenin Constituents of Five Primulaceous Plants
- On the Iridoid Constituent isolated from the Roots of Scrophularia buergeriana MIQ.
- Marine Natural Products. XXXIV. Trisindoline, a New Antibiotic Indole Trimer, Produced by a Bacterium of Vibrio sp. Separated from the Marine Sponge Hyrtios altum
- Indonesian Medicinal Plants. VI. On the Chemical Constituents of the Bark of Picrasma javanica BL. (Simaroubaceae) from Flores Island. Absolute Stereostructures of Picrajavanins A and B
- Marine Natural Products. X. Pharmacologically Active Glycolipids from the Okinawan Marine Sponge Phyllospongia foliascens (PALLAS)
- Foliaspongin, an Antiinflammatory Bishomosesterterpene from the Marine Sponge Phyllospongia foliascens (PALLAS)
- Studies on the chemical Modification of Monensin. III. Synthesis and Sodium Ion transport Activity of macrocylic Monenslamino Acid-1,29-lactones
- DEHATRINE, AN ANTIMALARIAL BISBENZYLISOQUINOLINE ALKALOID FROM THE INDONESIAN MEDICINAL PLANT BEILSCHMIEDIA MADANG, ISOLATED AS A MIXTURE OF TWO ROTATIONAL ISOMERS
- Solubilization of Saponins of Bupleuri Radix with Ginseng Saponins : Effect of Malonyl-ginsenosides on Water Solubility of Saikosaponin-b
- Indonesian Medicinal Plants. V. Chemical Structures of Calotroposides C, D, E, F, and G, Five Additional New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae)
- Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides
- Indonesian Medicinal Plants. I. Chemical Structures of Calotroposides A and B, Two New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae)
- Saponin and Sapogenol. L. On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Xinjiang, China. Chemical Structures of Licorice-Saponin L3 and Isoliquiritin Apioside
- LICORICE-SAPONINS F3,G2,H2,J2,AND K2,FIVE NEW OLEANENE-TRITERPENE OLIGOGLYCOSIDES FROM THE ROOT OF GLYCYRRHIZA URALENSIS
- Saponin and Sapogenol. XLIX. On the Constitutents of the Roots of Glycyrrhiza inflata BATALIN from Xinjiang, China. Characterization of Two Sweet Oleanane-Type Triterpene Oligoglycosides, Apioglycyrrhizin and Araboglycyrrhizin
- Saponin and Sapogenol. XLVIII. On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Northeastern China. (2).Licorice-saponins D3,E2,F3,G2,H2,J2,and K2
- MAMMOSIDES B AND H1,NEW IONOPHORIC RESIN-GLYCOSIDES FROM THE TUBER OF MERREMIA MAMMOSA, AN INDONESIAN FOLK MEDICINE
- APIOGLYCYRRHIZIN AND ARABOGLYCYRRHIZIN, TWO NEW SWEET OLEANENE-TYPE TRITERPENE OLIGOGLYCOSIDES FROM THE ROOT OF GLYCYRRHIZA INFLATA
- LICORICE-SAPONINS A3,B2,C2,D3,AND E2,FIVE NEW OLEANENE-TYPE TRITERPENE OLIGOGLYCOSIDES FROM CHINESE GLYCYRRHIZAE RADIX
- Saponin and Sapogenol. XLVII.On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Northeastern China. (1). Licorice-Saponins A3,B2,and C2
- Chemical Studies on Crude Drug Processing. VII. On the Constituents of Rehmanniae Radix. (1) : Absolute Stereostructures of Rehmaglutins A, B, and D Isolated from Chinese Rehmanniae Radix, the Dried Root of Rehmannia glutinosa LIBOSCH.
- Chemical Studies on Crude Drug Processing. VI. : Chemical Structures of Malonyl-ginsenosides Rb_1,Rb_2,Rc, and Rd Isolated from the Root of Panax ginseng C. A. MEYER
- Saponin and Sapogenol. XLIII. : Acetyl-soyasaponins A_4,A_5,and A_6,New Astringent Bisdesmosides of Soyasapogenol A, from Japanese Soybean, the Seeds of Glycine max MERRILL.
- Saponin and Sapogenol. XLII. : Structures of Acetyl-soyasaponins A_1,A_2,and A_3,Astringent Partially Acetylated Bisdesmosides of Soyasapogenol A, from American Soybean, the Seeds of Glycine max MERRILL.
- Saponin and Sapogenol. XLI. : Reinvestigation of the Structures of Soyasapogenols A, B, and E, Oleanene-Sapogenols from Soybean. Structures of Soyasaponins I, II, and III
- MALONYL-GINSENOSIDES Rb_1,Rb_2,Rc, AND Rd, FOUR NEW MALONYLATED DAMMARANE-TYPE TRITERPENE OLIGOGLYCOSIDES FROM GINSENG RADIX
- Saponin and Sapogenol. XXXVI. Chemical Constituents of Astragali Radix, the Root of Astragalus membranaceus BUNGE. (3). Astragalosides III, V, and VI
- Saponin and Sapogenol. XXXV. Chemical Constituents of Astragali Radix, the Root of Astragalus membranaceus BUNGE. (2). Astragalosides I, II and IV, Acetylastragaloside I and Isoastragalosides I and II
- Saponin and Sapogenol. XXXIII. Chemical Constituents of the Seeds of Vigna angularis (WILLD.) OHWI et OHASHI. (3). Azukisaponins V and VI
- Saponin and Sapogenol. XXXII. Chemical Constituents of the Seeds of Vigna angularis (WILLD.) OHWI et OHASHI. (2). Azukisaponins I, II, III, and IV
- Saponin and Sapogenol. XXXI. Chemical Constituents of the Seeds of Vigna angularis (WILLD.) OHWI et OHASHI. (1). Triterpenoidal Sapogenols and 3-Furanmethanol β-D-Glucopyranoside
- Saponin and Sapogenol. XXXIX. Structure of Soyasaponin A_1,a Bisdesmoside of Soyasapogenol A, from Soybean, the Seeds of Glycine max MERRILL
- Saponin and Sapogenol. XXXVIII. Structure of Soyasaponin A_2,a Bisdesmoside of Soyasapogenol A, from Soybean, the Seeds of Glycine max MERRILL
- REVISED STRUCTURES OF SOYASAPOGENOLS A, B, AND E, OLEANENE-SAPOGENOLS FROM SOYBEAN. STRUCTURES OF SOYASAPONINS I, II, AND III
- PULOSARIOSIDE, A NEW BITTER TRIMERIC-IRIDOID DIGLUCOSIDE, FROM AN INDONESIAN JAMU : THE BARK OF ALYXIA REINWARDTII BL__=. : APOCYNACEAE
- ABSOLUTE CONFIGURATIONS OF REHMAIONOSIDES A, B, AND C AND REHMAPICROSIDE THREE NEW IONONE GLUCOSIDES AND A NEW MONOTERPENE GLUCOSIDE FROM REHMANNIAE RADIX
- SYNTHESIS OF (-)-ARISTEROMYCIN FROM D-GLUCOSE
- SYNTHESES OF (+)-CYCLARADINE AND (+)-9-PSEUDO-β-L-XYLOFURANOSYLADENINE, TWO OPTICALLY ACTIVE CYCLOPENTANE ANALOGS OF NUCLEOSIDE
- A NEW APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE CYCLOHEXANE ANALOGS OF NUCLEOSIDE USING A MICHAEL-TYPE ADDITION REACTION TO NITRO-CYCLOHEXENES AS A KEY REACTION
- SYNTHESES OF VALIDAMINE : ___--VALIDAMINE, AND VALIENAMINE, THREE OPTICALLY ACTIVE ___--AMINO-SUGARS, FROM D-GLUCOSE
- SYNTHESES OF ___--α-D-ARABINOFURANOSE, ___--β-D-ARABINOFURANOSE, AND ___--β-L-XYLOFURANOSE, THREE OPTICALLY ACTIVE ___--PENTOFURANOSES, FROM D-GLUCOSE
- SYNTHESES OF ___--α-D-GLUCOPYRANOSE AND ___--β-L-IDOPYRANOSE, TWO OPTICALLY ACTIVE ___--HEXOPYRANOSES, FROM D-GLUCOSE BY USING STEREOSELECTIVE ERDUCTIVE DEACETOXYLATION WITH SODIUM BOROHYDRIDE AND CYCLITOL FORMATION FROM NITROFURAN
- SYNTHESIS OF DIBEKACIN (3',4'-DIDEOXYKANAMYCIN B) FROM D-GLUCOSAMINE AND D-GLUCOSE(Communication to the Editor)
- Saponin and Sapogenol. XX. Selective Cleavage of the Glucuronide Linkage in Saponin by Acetic Anhydride and Pyridine Treatment
- Saponin and Sapogenol. XIX. Selective Cleavage of the Glucuronide Linkage in Saponin by Lead Tetraacetate Oxidation followed by Alkali Treatment
- Saponin and Sapogenol. XVII. Structure of Sakuraso-saponin, a Pentaglycoside of Protoprimulagenin A from the Root of Primula sieboldi E. MORREN
- Chemical Transformation of Uronic Acids leading to Aminocyclitols. III. Syntheses of Aminocyclitols and Aminocyclitol-oligoglycosides from Uronic Acids and Glucuronide-saponins by Means of Electrolytic Decarboxylation
- Saponin and Sapogenol. XXIV. The Structure of Mi-Saponin C, a Bisdesmoside of Protobassic Acid from the Seed Kernels of Madhuca longifolia (L.) MACBRIDE
- Chemical Transformation of Uronic Acids Leading to Aminocyclitols. V. Syntheses of Aminocyclitol-oligosides from Glucuronide-saponins by Means of Lead Tetraacetate Oxidation
- Chemical Transformation of Uronic Acids leading to Aminocyclitols. IV. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine by Means of Electrolytic Decarboxylation
- FOUR NEW BISABOLENE-TYPE AMINOSESQUITERPENES FROM AN OKINAWAN MARINE SPONGE, THEONELLA SP(THEONELLIDAE)(Communications to the Editor)
- STRUCTURES OF MERREMOSIDES B AND D, NEW ANTISEROTONIC RESIN-GLYCOSIDES FROM THE TUBER OF MERREMIA MAMMOSA, AN INDONESIAN FOLK MEDICINE
- STRUCTURES OF SARASINOSIDES A_1, B_1, AND C_1 : NEW NORLANOSTANE-TRITERPENOID OLIGOGLYCOSIDES FROM THE PALAUAN MARINE SPONGE ASTEROPUS SARASINOSUM(Communications to the Editor)
- FOUR NEW LIPO-ALKALOIDS FROM ACONITI TUBER
- Saponin and Sapogenol. XL. Structure of Sophoraflavoside I, a Bisdesmoside of Soyasapogenol B, from Sophorae Radix, the Root of Sophora flavescens AITON
- CAPILLARTEMISIN A AND B, TWO NEW CHOLERETIC PRINCIPLES FROM ARTEMISIAE CAPILLARIS HERBA
- CHEMICAL MODIFICATION OF OLEANENE-OLIGOGLYCOSIDES BY MEANS OF ANODIC OXIDATION
- Saponin and Sapogenol. VIII. Photochemical Cleavage of Glycoside Linkage in Saponin. (1). Photolysis of Some Saponins and Their Structural Features
- Chemical Transformation of Uronic Acids leading to Aminocyclitols. II. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine
- Saponin and Sapogenol. XXIII. Degradation of Methyl Glucuronide and Methyl Galacturonide by Lead Tetraacetate Oxidation followed by Alkali Treatment
- Saponin and Sapogenol. XXXVII. Chemical Constituents of Astragali Radix, the Root of Astragalus membranaceus BUNGE. (4). Astragalosides VII and VIII
- Saponin and Sapogenol. XXIX. Selective Cleavage of the Glucuronide Linkage in Oligoglycosides by Anodic Oxidation
- ABSOLUTE STEREOSTRUCTURES OF REHMAGLUTIN C AND GLUTINOSIDE A NEW IRIDOID LACTONE AND A NEW CHLORINATED IRIDOID GLUCOSIDE FROM CHINESE REHMANNIAE RADIX
- Oxygen-Functionalization of C_-Angular Methyl Group in Pregnane Steroid by Means of Intramolecular Carbonyl-Mediated Anodic Oxidation