Secondary metabolites from Andrographis paniculata.

Abstract:

:Two new flavonoid glycosides, 5-hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-beta-D-glucopyranoside (1) and 5-hydroxy-7,8,2',5'-tetramethoxy-flavone-5-O-beta-D-glucopyranoside (2), and a new diterpenoid, andrographic acid (3), along with andrographidine A (4) were isolated from Andrographis paniculata, and their structures were determined on the basis of physicochemical and spectroscopic analysis. Compound 3 was evaluated for cytotoxicity to KB cells along with andrographolide, isoandrographolide, neoandrographolide and 14-deoxy-11,12-didehydroandrographolide obtained from A. paniculata in the present study. Cytotoxicity was observed for andrographolide and isoandrographolide with ED50 values of 6.5 and 5.1 microg/ml, respectively.

authors

Li W,Xu X,Zhang H,Ma C,Fong H,van Breemen R,Fitzloff J

doi

10.1248/cpb.55.455

subject

Has Abstract

pub_date

2007-03-01 00:00:00

pages

455-8

issue

3

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/55.455

journal_volume

55

pub_type

杂志文章
  • Analgesic components from bornean medicinal plants, Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir.

    abstract::The analgesic components were isolated from a Bornean medicinal plant, Tabernaemontana pauciflora Blume (syn. Ervatamia blumeana Mark gr.), and the major components were identified as coronaridine and 3-(2-oxopropyl)coronaridine. Four minor components were estimated to be 5R- and 5S-(2-oxopropyl)coronaridine, 3-(2-oxo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2075

    authors: Okuyama E,Gao LH,Yamazaki M

    更新日期:1992-08-01 00:00:00

  • Preparation of benzo[b]furans having five-membered heterocycles at the 2-position and 2-(4-Alkylcarbamoylbuta-1,3-dienyl)benzo[b]furans, and their cysteinyl leukotriene receptor (cysLT1, cysLT2) inhibitory activity.

    abstract::A series of benzo[b]furan derivatives having a five-membered heterocyclic substituent at the 2-position were prepared from 2-(1-chloro-2-formylvinyl)benzo[b]furans (2) and 2-(4-alkylcarbamoylbuta-1,3-dienyl)benzo[b]furans. These 2-heterocyclic benzo[b]furans were evaluated for their cysteinyl leukotriene receptor (cys...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00560

    authors: Akai Y,Tabuchi Y,Ando K,Ito A,Sakata Y,Kawasaki I,Ohishi T,Yamashita M,Ohta S,Nishide K,Ohishi Y

    更新日期:2012-01-01 00:00:00

  • Development of Supramolecular Saccharide Sensors Based on Cyclodextrin Complexes and Self-assembling Systems.

    abstract::Cyclodextrins (CDs) are water-soluble host compounds having nano-size hydrophobic cavities that enable them to incorporate organic molecules in water. Optically inert CDs can be efficiently combined with various types of chromoionophores and fluoroionophores. In this study, using diverse combinations of phenylboronic ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c16-00963

    authors: Tsuchido Y,Fujiwara S,Hashimoto T,Hayashita T

    更新日期:2017-01-01 00:00:00

  • Proton nuclear magnetic resonance studies of the complexation of zinc(II) with glycyl-L-histidylglycine.

    abstract::The complexation of Zn(II) with glycyl-L-histidylglycine and its deuterated derivatives, glycyl-d2-L-histidylglycine and glycyl-L-histidylglycine-d2, was studied by proton nuclear magnetic resonance spectroscopy over the pD range, from 3.4 to 11.0, at 25 degrees C. Addition of Zn(II) to the peptide made the resonances...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.2042

    authors: Ueda J,Hanaki A,Yoshida N,Nakajima T

    更新日期:1995-12-01 00:00:00

  • Synthesis of optically active NC-1800, a therapeutic agent for urinary disturbance.

    abstract::A new synthetic method for chiral oxazolidinone derivatives, therapeutic agents for treating urinary disturbance, is described. The condensed compound obtained from chiral 1-amino-3-phenyl-2-propanol and 1-phenyl-3-morpholino-1-propanone was reduced with Me4NBH(OAc)3 to give the intermediate, 1-(3-morpholino-1-phenylp...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1154

    authors: Yoshida S,Yamamoto M,Mochizuki N,Nohira H

    更新日期:1999-08-01 00:00:00

  • Characteristics of hyaluronate-hydroxyethyl acrylate blend gel and release of cationic amphiphilic solutes.

    abstract::Hyaluronate-hydroxyethyl acrylate blend gel (HA-PHEA) were prepared to modify the brittleness of hyaluronate gel (HA) and the characteristics of HA-PHEA gel were compared with those of HA and polyhydroxyethyl acrylate (PHEA) gels. These gels were high in water content and transparent. HA-PHEA gel was improved in visco...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1341

    authors: Jin Y,Yamanaka J,Sato S,Miyata I,Yomota C,Yonese M

    更新日期:2002-10-01 00:00:00

  • Bile salt-induced disintegration of egg phosphatidylcholine liposomes: a kinetic study based on turbidity changes.

    abstract::The disintegration kinetics of egg phosphatidylcholine small unilamellar liposomes in various bile salts (nine species) were investigated by monitoring turbidity changes with a stopped-flow apparatus. The pseudo-first-order rate constants obtained as a function of bile salt concentration (up to 25 mM) were analyzed ba...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1341

    authors: Nagata M,Yotsuyanagi T,Ikeda K

    更新日期:1990-05-01 00:00:00

  • Total synthesis of biologically active natural products based on highly selective synthetic methodologies.

    abstract::Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-Baylis-Hillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c14-00474

    authors: Hatakeyama S

    更新日期:2014-01-01 00:00:00

  • Aromaticity of Phenylalanine Residues Is Essential for Amyloid Formation by Alzheimer's Amyloid β-Peptide.

    abstract::The abnormal aggregation of amyloid β-peptide (Aβ) is central to the pathogenesis of Alzheimer's disease, the major form of dementia. Aromatic π-π interactions have been suggested to play a crucial role in the aggregation of not only Aβ, but also other amyloidogenic proteins. In this study, each or all phenylalanine (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00203

    authors: Genji M,Yano Y,Hoshino M,Matsuzaki K

    更新日期:2017-01-01 00:00:00

  • Efficient synthesis of a key intermediate of DV-7751 via optical resolution or microbial reduction.

    abstract::Two efficient and practical methods of synthesis of the C-10 substituent of DV-7751 (1), a novel quinolone carboxylic acid, were established. The first method utilizes an optical resolution of racemic 8-amino-6-benzyl-6-azaspiro[3.4]octane (13), while the second employs an enantioselective microbial reduction of 6-ben...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.563

    authors: Miyadera A,Satoh K,Imura A

    更新日期:2000-04-01 00:00:00

  • Interaction of polyphenolic metabolites with human serum albumin: a circular dichroism study.

    abstract::Binding sites of polyphenolic compounds on human serum albumin (HSA) were investigated using induced Cotton effects on the circular dichroism (CD) spectra. Polyphenolic compounds used in this study are known to be metabolites from tannins and their related polyphenols in food and medicinal plants. The present investig...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1019

    authors: Nozaki A,Kimura T,Ito H,Hatano T

    更新日期:2009-09-01 00:00:00

  • QSPR prediction of aqueous solubility of drug-like organic compounds.

    abstract::A quantitative structure property relationship (QSPR) study was performed to develop a model that relates the structures of 150 drug organic compounds to their aqueous solubility (log S(w)). Molecular descriptors derived solely from 3D structure were used to represent molecular structures. A subset of the calculated d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.669

    authors: Ghasemi J,Saaidpour S

    更新日期:2007-04-01 00:00:00

  • Synthesis and biological evaluation of peptide mimics derived from first extracellular loop of CCR5 toward HIV-1.

    abstract::Peptide mimics derived from the first extracellular loop of CCR5 bearing non-peptide spacers in place of Ala-Ala-Ala sequence in the peptide moiety were synthesized, and the effects of these compounds on the inhibition against HIV-1 were examined. Compound 2b having m-aminophenoxyacetic acid derivative as a non-peptid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1479

    authors: Ikeda K,Ishii Y,Konishi K,Sato M,Tanaka K

    更新日期:2004-12-01 00:00:00

  • [2-(omega-phenylalkyl)phenoxy]alkylamines: synthesis and dual dopamine2 (D2) and 5-hydroxytryptamine2 (5-HT2) receptor antagonistic activities.

    abstract::A series of [2-(omega-phenylalkyl)phenoxy]alkylamines was synthesized and their 5-hydroxytryptamine2 (5-HT2) and/or dopamine2 (D2) receptor antagonistic activities were examined in vitro. [2-(4-Phenylbutyl)phenoxy]alkylamines showed strong inhibition of both 5-HT2 and D2 receptors. In particular, [2-(4-Phenylbutyl)phe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.639

    authors: Tanaka N,Goto R,Ito R,Hayakawa M,Ogawa T,Fujimoto K

    更新日期:1998-04-01 00:00:00

  • Three new diterpenoid alkaloids from roots of Aconitum ouvrardianum HAND.-MAZZ.

    abstract::A new C(19)-diterpenoid alkaloid, ouvrardiantine (1) and two new C(20)-diterpenoid alkaloids, ouvrardiandines A (2) and B (3) were isolated from the root of Aconitum ouvrardianum HAND.-MAZZ. The structure of the new alkaloids was established on the basis of spectral data (1D- and 2D-NMR, HR-MS). ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1090

    authors: Hou LH,Chen DL,Jian XX,Wang FP

    更新日期:2007-07-01 00:00:00

  • Cytotoxic activity and DNA-binding properties of isoeuxanthone derivatives.

    abstract::In this study, the interactions of different groups substituted isoeuxanthone derivatives with calf thymus DNA (ct DNA) were investigated by spectrophotometric methods and viscosity measurements. Results indicated that the xanthone derivatives could intercalate into the DNA base pairs by the plane of xanthone ring and...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00789

    authors: Wang HF,Yan H,Gao X,Niu B,Guo R,Wei L,Xu B,Tang N

    更新日期:2014-01-01 00:00:00

  • Ginseng Saponins in Different Parts of Panax vietnamensis.

    abstract::Chemical and pharmacological studies of Panax vietnamensis (Vietnamese ginseng; VG) have been reported since its discovery in 1973. However, the content of each saponin in different parts of VG has not been reported. In this study, 17 ginsenosides in the different underground parts of P. vietnamensis were analyzed by ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00369

    authors: Le TH,Lee GJ,Vu HK,Kwon SW,Nguyen NK,Park JH,Nguyen MD

    更新日期:2015-01-01 00:00:00

  • Studies towards the synthesis of the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid: improved synthesis of the base beta-hydroxywybutine.

    abstract::An improved synthesis of the key intermediates (3 and 8) for the synthesis of beta-hydroxywybutines [[R-(R*,S*)]- and [S-(R*,R*)]-4], the most probable structures for the minor base from rat liver tRNA(Phe), has been achieved by the Wittig reaction between 1-benzyl-7-formylwye (1) and the phosphorane derived from (R)-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1220

    authors: Itaya T,Kanai T

    更新日期:1998-08-01 00:00:00

  • Structures and solid state tautomeric forms of two novel antileukemic tropoloisoquinoline alkaloids, pareirubrines A and B, from Cissampelos pareira.

    abstract::Two novel tropoloisoquinoline alkaloids, Pareirubrines A and B, have been isolated as antileukemic substances from Cissampelos pareira (Menispermaceae), together with the same skeleton alkaloids, grandirubrine and isoimerubrine. Their structures were elucidated by nuclear magnetic resonance (NMR) studies, and their so...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1418

    authors: Morita H,Matsumoto K,Takeya K,Itokawa H,Iitaka Y

    更新日期:1993-08-01 00:00:00

  • 1,4:3,6-Dianhydrohexitol nitrate derivatives. II. Synthesis and antianginal activity of aryl- or arylcarbonylpiperazine derivatives.

    abstract::A series of 5-(4-aryl- or 4-arylcarbonylpiperazin-1-yl)-5-deoxy-1,4: 3,6-dianhydro-L-iditol 2-nitrates was prepared in order to obtain orally active, nitrate-type vasodilators with reduced side effects. Our drug design was based on a small reduction in the lipophilicity compared to that of 5-deoxy-5-[4-(3-phenylthiopr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1100

    authors: Hayashi H,Ikeda J,Kubo K,Moriyama T,Karasawa A,Suzuki F

    更新日期:1993-06-01 00:00:00

  • Studies on cardiotonic agents. II. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives.

    abstract::A series of phthalazine and 1,2,3-benzotriazine derivatives which have heterocyclylpiperidino groups was synthesized and tested for cardiotonic activity in anesthetized dogs. Several 6,7-dimethoxyphthalazine derivatives showed relatively potent cardiotonic activity comparable to that of amrinone. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2179

    authors: Nomoto Y,Obase H,Takai H,Teranishi M,Nakamura J,Kubo K

    更新日期:1990-08-01 00:00:00

  • Three New Polyphenolic Acids from the Leaves of Eucalyptus citriodora with Antivirus Activity.

    abstract::Six polyphenolic acids (1-6), including the three new compounds citriodolic acids A, B, and C (1-3), were isolated from the leaves of Eucalyptus citriodora. Their structures were elucidated by spectroscopic methods including one dimensional (1D)- and 2D-NMR, high-resolution electrospray ionization (HR-ESI)-MS, and cir...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00362

    authors: Lin SQ,Zhou ZL,Yin WQ

    更新日期:2016-11-01 00:00:00

  • Ebenamariosides A-D: Triterpene Glucosides and Megastigmanes from the Leaves of Diospyros maritima.

    abstract::The 1-BuOH-soluble fraction of the methanol (MeOH) extract of Diospyros maritima was separated by chromatographic techniques to give three new oleanane-type and one new ursane-type triterpene glucoside, named ebenamariosides A-D (1-4); two megastigmanes were also isolated. The structures of triterpene glucosides was e...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00803

    authors: Kawakami S,Miura E,Nobe A,Inagaki M,Nishimura M,Matsunami K,Otsuka H,Aramoto M

    更新日期:2019-01-01 00:00:00

  • Acridine derivatives. III. Preparation and antitumor activity of the novel acridinyl-substituted uracils.

    abstract::In an investigation of a new class of deoxyribonucleic acid (DNA)-intercalating antitumor agents, novel acridinyl-substituted uracils have been synthesized and evaluated for activity against L1210 leukemia in vivo, and against bacteria and fungus. These compounds were prepared by the novel enamine reaction between 9-c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.697

    authors: Kimura M,Okabayashi I,Kato A

    更新日期:1989-03-01 00:00:00

  • Superoxide dismutase activity of iron(II)TPEN complex and its derivatives.

    abstract::Superoxide is involved in the pathogenesis of various diseases, such as inflammation, ischemia-reperfusion injury and carcinogenesis. Superoxide dismutases (SODs) catalyze the disproportionation reaction of superoxide to produce oxygen and hydrogen peroxide, and can protect living cells against the toxicity of free ra...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1514

    authors: Tamura M,Urano Y,Kikuchi K,Higuchi T,Hirobe M,Nagano T

    更新日期:2000-10-01 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

  • Lipid peroxidation of the erythrocyte membrane caused by stimulated polymorphonuclear leukocytes in the presence of ferritin.

    abstract::Lipid peroxidation of erythrocyte membrane was caused by phorbol myristate acetate (PMA)-stimulated polymorphonuclear leukocytes (PMN) in the presence of ferritin. PMN themselves were not peroxidized. A lag period was observed before the start of the peroxidation reaction. In contrast, ferritin iron was continuously r...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1507

    authors: Miura T,Ogiso T

    更新日期:1991-06-01 00:00:00

  • Synthesis and antitumor activity of new alkylphospholipids containing modifications of the phosphocholine moiety.

    abstract::New antitumor alkylglycerophospholipids, in which primarily the phosphocholine moiety of the platelet activating factor (PAF) molecule was modified, were synthesized from 1-alkyl-2-substituted glycerols by introducing polar head phosphoryl groups having methylene bridges of various lengths (from 2 to 14 carbons). They...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1249

    authors: Ukawa K,Imamiya E,Yamamoto H,Mizuno K,Tasaka A,Terashita Z,Okutani T,Nomura H,Kasukabe T,Hozumi M

    更新日期:1989-05-01 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

  • Effect of metal ions on transcription of the ada gene which encodes O6-methylguanine-DNA methyltransferase of Escherichia coli.

    abstract::The effect of metal ions on transcription of the ada gene of Escherichia coli which is promoted by Ada protein in the presence of methylated deoxyribonucleic acid (DNA) was examined in a reconstituted system. Their effect on the O6-methylguanine-DNA methyltransferase (MGTase) activity of Ada protein was also examined....

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2483

    authors: Takahashi K,Suzuki M,Sekiguchi M,Kawazoe Y

    更新日期:1992-09-01 00:00:00