CHEMICAL MODIFICATION OF OLEANENE-OLIGOGLYCOSIDES BY MEANS OF ANODIC OXIDATION

スポンサーリンク

概要

• 論文の詳細を見る

• By utilizing anodic oxidation as the key reaction, various olean-12-ene sapogenols were readily converted into olean-11-en-28,13β-olide, 11α, 12α-epoxy-oleanan-28,13β-olide, and 13β, 28-epoxy-olean-11-ene derivatives, respectively in high yields. Since previous protection of hydroxyl groups in the starting compounds was not required, the conversion method was directly applied to hederagenin oligoglycosides and corresponding oligoglycosides of olean-11-ene sapogenols, functionalized as above, were successfully synthesized.

• 公益社団法人日本薬学会の論文
• 1982-08-25

著者

• 吉川 雅之

  Faculty of Pharmaceutical Sciences, Osaka University

• 北川 勲

  Faculty Of Pharmaceutical Sciences Osaka University

• 王 恵康

  Department Of Chinese Material Medica Shanghai College Of Traditional Chinese Medicine

• 王 恵康

  Faculty of Pharmaceutical Sciences, Osaka University

• Tosirisuk Veeraphan

  Faculty of Pharmaceutical Sciences, Osaka University

• Tosirisuk Veeraphan

  Faculty Of Pharmaceutical Sciences Osaka University

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

もっと見る 閉じる

スポンサーリンク