Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis Fischer from northeastern China. (1). Licorice-saponins A3, B2, and C2.

Abstract:

:From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-beta-D-glucopyranosylglycyrrhizin, 11-deoxo-glycyrrhizin, and 3-O-[beta-D-glucuronpyranosyl(1-->2)-beta-D-glucuronpyranosyl++ +]oleana- 11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizin (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

authors

Kitagawa I,Hori K,Taniyama T,Zhou JL,Yoshikawa M

doi

10.1248/cpb.41.43

subject

Has Abstract

pub_date

1993-01-01 00:00:00

pages

43-9

issue

1

eissn

0009-2363

issn

1347-5223

journal_volume

41

pub_type

杂志文章
  • Effect of Drug Combination on Omeprazole Metabolism by Cytochrome P450 2C19 in Helicobacter pylori Eradication Therapy.

    abstract::Helicobacter pylori (H. pylori) infection is common and can result in gastric and duodenal ulcers, and in some cases, gastric lymphoma and cancer. Omeprazole (OMP)-in combination with clarithromycin (CLR), amoxicillin (AMX), tinidazole (TND), or metronidazole (MET)-is used in double or triple combination therapy for e...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00084

    authors: Attia TZ,Yamashita T,Tsujino H,Derayea SM,Tsutsumi Y,Uno T

    更新日期:2019-01-01 00:00:00

  • Phenylpropanoid glycosides from Rhodiola rosea.

    abstract::Rhodiola rosea L. (Golden Root) has been used for a long time as an adaptogen in Chinese traditional medicine and is reported to have many pharmacological properties. Along its known secondary metabolites tyrosol (1), salidroside (rhodioloside) (2), rosin (3), rosarin (4), rosavin (5), sachaliside 1 (6) and 4-methoxy-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.467

    authors: Tolonen A,Pakonen M,Hohtola A,Jalonen J

    更新日期:2003-04-01 00:00:00

  • Rhyncosides A-F, phenolic constituents from the Chinese mangrove plant Bruguiera sexangula var. rhynchopetala.

    abstract::Chemical investigation on the stem of a Chinese mangrove plant Bruguiera sexangula var. rhynchopetala (Rhizophoraceae) resulted in the isolation and characterization of four new phenolic glycosides rhyncosides A-D (1-4), and two new lignan derivatives namely rhyncosides E-F (5-6), along with twelve known phenolic cons...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1175

    authors: Bao S,Ding Y,Deng Z,Proksch P,Lin W

    更新日期:2007-08-01 00:00:00

  • Marine natural products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum.

    abstract::A new antibiotic indole trimer named trisindoline (1) was isolated, together with a known dioxopiperazine brevianamide F (2), from the culture of a bacterium of Vibrio sp., which was separated from the Okinawan marine sponge Hyrtios altum. The structure of trisindoline (1) has been determined on the bases of physicoch...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.2449

    authors: Kobayashi M,Aoki S,Gato K,Matsunami K,Kurosu M,Kitagawa I

    更新日期:1994-12-01 00:00:00

  • α-Heteroarylation of ketones via the umpolung reaction of N-alkoxyenamine.

    abstract::A new method has been developed for the umpolung α-heteroarylation of ketones via an N-alkoxyenamine. The treatment of ketones with tris(heteroaryl)aluminum reagents in the presence of isoxazolidine gave the corresponding α-heteroarylated ketones in moderate to good yields. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00404

    authors: Miyoshi T,Takeda N,Fukami M,Sato S,Ueda M,Miyata O

    更新日期:2014-01-01 00:00:00

  • Triterpenoid saponins from the seeds of Pharbitis nil.

    abstract::From the seeds of Pharbitis nil (Convolvulaceae), two new oleanene-type triterpene glycosides, pharbitosides A (1) and B (2), together with beta-sitosterol, beta-sitosterol glucoside (daucosterol), caffeic acid, and methyl caffeate were isolated. The structure of pharbitoside A (1) was elucidated to be queretaroic aci...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.203

    authors: Jung DY,Ha H,Lee HY,Kim C,Lee JH,Bae K,Kim JS,Kang SS

    更新日期:2008-02-01 00:00:00

  • Catalytic activity of anion-exchange resins modified with metal-porphine in oxidative reactions of phenols.

    abstract::Anion-exchange resins modified with metal-porphine (M-Pr) have been investigated to develop a solid catalyst in the oxidative reaction of phenols by O2 in air. Co-Pr, which is easily prepared and separable from the reaction mixture, has been proved to accelerate the oxidative reaction of phenols such as 3,5-di-tertbut...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1831

    authors: Iwado A,Mifune M,Kato J,Oda J,Chikuma M,Motohashi N,Saito Y

    更新日期:2000-11-01 00:00:00

  • Spiro-substituted piperidines as neurokinin receptor antagonists. I. Design and synthesis of (+/-)-N-[2-(3,4-dichlorophenyl)-4-(spiro [isobenzofuran-1(3H),4'piperidin]-1'-yl)butyl]-N-methylbenzamide, YM-35375, as a new lead compound for novel neurokinin r

    abstract::Analysis of the structural requirements of compound 1 (SR48968), a potent NK2 receptor antagonist, revealed that the 4-phenyl group of the piperidine is essential for binding with the NK2 receptor and occupies an equatorial position. Energy calculation of a variety of substituted 4-phenyl piperidines revealed that spi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.351

    authors: Kubota H,Fujii M,Ikeda K,Takeuchi M,Shibanuma T,Isomura Y

    更新日期:1998-02-01 00:00:00

  • Synthesis and antidiuretic activities of novel glycoconjugates of arginine-vasopressin.

    abstract::Arginine-vasopressin (AVP) was acylated with various acyl azides (2a-j) in pH 9.1 buffer to give AVP derivatives (11a-j) modified at the tyrosine side chain with a carbohydrate via a spacer arm. Glycoconjugates of AVP modified at the N-terminal amide (12a-e) were also synthesized from AVP and carboxylic acids (3a-e) u...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1530

    authors: Susaki H,Suzuki K,Ikeda M,Yamada H,Watanabe HK

    更新日期:1998-10-01 00:00:00

  • 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).

    abstract::The synthetic route for 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), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1018

    authors: Yanagi T,Kikuchi K,Takeuchi H,Ishikawa T,Nishimura T,Yamamoto I

    更新日期:2001-08-01 00:00:00

  • Aglaiabbrevins A-D, New Prenylated Bibenzyls from the Leaves of Aglaia abbreviata with Potent PTP1B Inhibitory Activity.

    abstract::Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl]bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were eluci...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00868

    authors: Sun P,Jiang CS,Zhang Y,Liu AH,Liang TJ,Li J,Guo YW,Jiang JM,Mao SC,Wang B

    更新日期:2017-01-01 00:00:00

  • Specific effect of polyunsaturated fatty acids on the cholesterol-poor membrane domain in a model membrane.

    abstract::To understand more fully the effect of polyunsaturated fatty acids (PUFAs) on lipid bilayers, we investigated the effects of treatment with fatty acids on the properties of a model membrane. Three kinds of liposomes comprising dipalmitoylphosphatidylcholine (DPPC), dioleylphosphatidylcholine (DOPC), and cholesterol (C...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1103

    authors: Onuki Y,Hagiwara C,Sugibayashi K,Takayama K

    更新日期:2008-08-01 00:00:00

  • Binding properties of adenosine deaminase interacted with theophylline.

    abstract::Thermodynamic studies were carried out to evaluate the binding of theophylline on adenosine deaminase (ADA) in 50 mM sodium phosphate buffer pH 7.5, at 300 K, using isothermal titration calorimetry (ITC). A simple method for determination of binding isotherm in the drug--ADA interaction was applied using ITC data. ADA...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1179

    authors: Saboury AA,Bagheri S,Ataie G,Amanlou M,Moosavi-Movahedi AA,Hakimelahi GH,Cristalli G,Namaki S

    更新日期:2004-10-01 00:00:00

  • Synergistic action of phenolic signal compounds and carbohydrates in the induction of virulence gene expression of Agrobacterium tumefaciens.

    abstract::Virulence (vir) gene expression of Agrobacterium tumefaciens is activated by plant phenolic compounds such as alpha-hydroxyacetosyringone (HOAS), acetosyringone (AS), methyl syringate, coniferyl alcohol and sinapyl alcohol. Inositol was found to be a potentiating factor of vir-inducing activity, which enhanced the vir...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2613

    authors: Song YN,Shibuya M,Ebizuka Y,Sankawa U

    更新日期:1991-10-01 00:00:00

  • Antioxidant constituents of Caragana tibetica.

    abstract::Caragana tibetica KOM. (Fabaceae) is a medicinal plant that has been traditionally used in western part of China. In the course of our screening study on antioxidant activity of medicinal plants, the 70% acetone extract of the stems of C. tibetica was found to have a potent superoxide anion scavenging activity. Tibeti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1204

    authors: Xiang T,Uno T,Ogino F,Ai C,Duo J,Sankawa U

    更新日期:2005-09-01 00:00:00

  • New neplanocin analogues. VIII. Synthesis and biological activity of 6'-C-ethyl, -ethenyl, and -ethynyl derivatives of neplanocin A.

    abstract::This report describes the synthesis and antiviral effects of (6'R)-6'-C-ethynyl, -ethenyl, and -ethyl derivatives of neplanocin A (7a, 8a, and 9a, respectively) and the corresponding 6'S-diastereomers (7b, 8b, and 9b, respectively), as examples of 6'-C-substituted analogues of neplanocin A. Grignard reaction of the 6'...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1163

    authors: Shuto S,Obara T,Saito Y,Yamashita K,Tanaka M,Sasaki T,Andrei G,Snoeck R,Neyts J,Padalko E,Balzarini J,De Clercq E,Matsuda A

    更新日期:1997-07-01 00:00:00

  • Effects of aging on crystallization, dissolution and absorption characteristics of amorphous tolbutamide-2-hydroxypropyl-beta-cyclodextrin complex.

    abstract::The effects of storage on the crystallization, dissolution and absorption of tolbutamide from amorphous tolbutamide-2-hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) complex were investigated, in comparison with those of polyvinylpyrrolidone (PVP) solid dispersion. The amorphous solid complex of tolbutamide with HP-beta...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.646

    authors: Kimura K,Hirayama F,Arima H,Uekama K

    更新日期:2000-05-01 00:00:00

  • Functional analysis of the iron(II) etiocorrphycene incorporated in the myoglobin heme pocket.

    abstract::The iron(III) complex of 2,7,12,17-tetraethyl-3,6,11,18-tetra-methylcorrphycene, an isomeric heme, was complexed with apomyoglobin to examine the ligand binding ability of the novel macrocycle under physiological conditions. The reconstituted holoprotein was found to be functionally active at pH 7.4 and 20 degrees C a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.345

    authors: Neya S,Nakamura M,Imai K,Funasaki N

    更新日期:2001-03-01 00:00:00

  • Pyrrole Oligoglycosides from the Starfish Acanthaster planci Suppress Lipopolysaccharide-Induced Nitric Oxide Production in RAW264.7 Macrophages.

    abstract::Two new pyrrole oligoglycosides, plancipyrrosides A and B (1 and 2), were isolated from methanol extract of the Vietnamese starfish Acanthaster planci using various chromatographic procedures. Their structures were elucidated by spectroscopic methods including one and two dimensional (1D- and 2D)-NMR and Fourier trans...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00585

    authors: Vien LT,Hanh TT,Huong PT,Dang NH,Thanh NV,Lyakhova E,Cuong NX,Nam NH,Kiem PV,Kicha A,Minh CV

    更新日期:2016-11-01 00:00:00

  • First synthesis of a alpha-trifluoromethyl allenol ether via the Julia-Lythgoe process.

    abstract::Alpha-trifluoromethyl allenol ethers 9a-e were prepared in moderate to good yields by the Julia-Lythgoe process using beta-ethoxy-beta-trifluoromethyl vinylic sulfone 3. Several reactions of 9c were examined to give alpha,beta-unsaturated trifluoromethyl ketone derivatives 11 and 12. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1395

    authors: Yoshimatsu M,Hibino M

    更新日期:2000-09-01 00:00:00

  • Prediction of color changes using the time-temperature superposition principle in liquid formulations.

    abstract::This study reports the results of applying the time-temperature superposition principle (TTSP) to the prediction of color changes in liquid formulations. A sample solution consisting of L-tryptophan and glucose was used as the model liquid formulation for the Maillard reaction. After accelerated aging treatment at ele...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00530

    authors: Mochizuki K,Takayama K

    更新日期:2014-01-01 00:00:00

  • Preparation and evaluation of sustained-release doxazosin mesylate pellets.

    abstract::Doxazosin mesylate (DXM) sustained release pellets were prepared by an extrusion-spheronization and fluid-bed coating technique. The core pellets containing DXM were prepared by extrusion-spheronization technique, and coated by a fluid-bed coater to control the release of DXM. The factors affecting to properties of pe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00767

    authors: Ha JM,Kim JY,Oh TO,Rhee YS,Chi SC,Kuk H,Park CW,Park ES

    更新日期:2013-01-01 00:00:00

  • Studies on cardiac ingredients of plants. IX. Chemical transformation of proscillaridin by utilizing its 1,4-cycloadducts as key compounds and biological activities of their derivatives.

    abstract::Three aromatic compounds (2-4) possessing a carbomethoxyl group or a dimethoxyphthaloyl group, prepared by the Diels-Alder reaction of the cardiac glycoside, proscillaridin (1), with dimethyl acetylenedicarboxylate and methyl propiolate, were transformed into alcohols, carboxylic acids and amides. The biological activ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.327

    authors: Tanase T,Murakami N,Nagai S,Ueda T,Sakakibara J,Ando H,Hotta Y,Takeya K

    更新日期:1992-02-01 00:00:00

  • Six new presenegenin glycosides, reiniosides A--F, from Polygala reinii root.

    abstract::Six new oleanane-type triterpene saponins, called reiniosides A-F, were isolated from the roots of Polygala reinii Fr. et Sav. and their structures were elucidated by spectroscopic and chemical means. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.466

    authors: Miyase T,Saitoh H,Shiokawa K,Ueno A

    更新日期:1995-03-01 00:00:00

  • Synthesis and evaluation of 6-nitro-7-(1-piperazino)quinazolines: dual-acting compounds with inhibitory activities toward both tumor necrosis factor-alpha (TNF-alpha) production and T cell proliferation.

    abstract::We investigated the chemical modifications of the nitroquinazoline derivative (1) through the replacement of the NH group at the C(4)-position with several N-alkyl groups to increase the lipophilicity at the C(4)-position. Among them, we found that the N-methyl analogue (5a) showed a 2-fold loss in the inhibitory acti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1109

    authors: Tobe M,Isobe Y,Tomizawa H,Nagasaki T,Aoki M,Negishi T,Hayashi H

    更新日期:2003-09-01 00:00:00

  • Transformation of metastable forms of acetaminophen studied by thermal Fourier transform infrared (FT-IR) microspectroscopy.

    abstract::A novel Fourier transform infrared (FT-IR) microspectroscopy equipped with a micro hot stage (thermal FT-IR microscopic system) was used to quickly study the phase transformation of acetaminophen polymorphs by a one-step process. Acetaminophen was sealed in KBr disc on the first and second heating processes under this...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.153

    authors: Wang SL,Lin SY,Wei YS

    更新日期:2002-02-01 00:00:00

  • Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol: a novel triglyceride from berries of Hippophae rhamnoides.

    abstract::1,3-Dicapryloyl-2-linoleoylglycerol (1), a novel triglyceride, was isolated from berries of Hippophae rhamnoides. The structure was elucidated on the basis of MS, 1D and 2D NMR experiments including HMQC and HMBC. The metal chelating, free radical scavenging, and lipid peroxidation inhibiting properties of the compoun...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1021

    authors: Swaroop A,Sinha AK,Chawla R,Arora R,Sharma RK,Kumar JK

    更新日期:2005-08-01 00:00:00

  • Uses of 1-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]-thiophen-2-yl)-3-dodecanoylthiourea as a Building Block in the Synthesis of Fused Pyrimidine and Thiazine Systems.

    abstract::The reaction of lauroyl isothiocyanate and 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile was used to synthesize the title compound 2. Compound 2 could serve as the main building block in the synthesis of many target heterocyclic systems. Various fused pyrimidines were synthesized in the reactions of compo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00047

    authors: Hemdan MM,Abd El-Mawgoude HK

    更新日期:2015-01-01 00:00:00

  • Possible mechanism of the stimulatory effect of Artemisia leaf extract on the proliferation of cultured endothelial cells: involvement of basic fibroblast growth factor.

    abstract::To investigate the possible mechanism of the stimulatory effect of a hot water extract from Artemisia leaf (Artemisia princeps PANPANINI) (AFE) on the proliferation of endothelial cells, cells from bovine aorta were cultured for 72 h in RPMI1640 medium supplemented with 10% fetal calf serum in the presence of 5 microg...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2494

    authors: Kaji T,Kaga K,Miezi N,Hayashi T,Ejiri N,Sakuragawa N

    更新日期:1990-09-01 00:00:00

  • Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs.

    abstract::The synthesis of acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorter, and the total yield was 4.5% greater than the previous synthe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.517

    authors: Uenishi J,Kobayashi N,Komine S,Okadai T,Yonemitsu O,Sasaki T,Yamada Y

    更新日期:1999-04-01 00:00:00