New triterpenoid saponins with strong alpha-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana.

Abstract:

:Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (2-4, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their alpha-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on alpha-glucosidase.

journal_name

Bioorg Med Chem

authors

Luo JG,Ma L,Kong LY

doi

10.1016/j.bmc.2007.12.053

subject

Has Abstract

pub_date

2008-03-15 00:00:00

pages

2912-20

issue

6

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)01123-6

journal_volume

16

pub_type

杂志文章
  • Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates.

    abstract::The two β-carbonic anhydrases (CAs, EC 4.2.1.1) from the bacterial pathogen Salmonella enterica serovar Typhimurium, stCA 1 and stCA 2, were investigated for their inhibition with a large panel of sulfonamides and sulfamates. Unlike inorganic anions, which are weak, millimolar inhibitors of the two enzymes [Vullo et a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.038

    authors: Nishimori I,Minakuchi T,Vullo D,Scozzafava A,Supuran CT

    更新日期:2011-08-15 00:00:00

  • Activation of lysine-specific demethylase 1 inhibitor peptide by redox-controlled cleavage of a traceless linker.

    abstract::We have previously employed cyclization of a linear peptide as a strategy to modulate peptide function and properties, but cleavage to regenerate the linear peptide left parts of the linker structure on the peptide, interfering with its activity. Here, we focused on cyclization of a linear peptide via a "traceless" di...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.033

    authors: Amano Y,Umezawa N,Sato S,Watanabe H,Umehara T,Higuchi T

    更新日期:2017-02-01 00:00:00

  • Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

    abstract::In the light of known HDAC inhibitors, 33 carboxylic acid derivatives were tested to understand the structural requirements for HDAC inhibition activity. Several modifications were applied to develop the structure-activity relationships of carboxylic acid HDAC inhibitors. HDAC inhibition activities were investigated i...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.042

    authors: Bora-Tatar G,Dayangaç-Erden D,Demir AS,Dalkara S,Yelekçi K,Erdem-Yurter H

    更新日期:2009-07-15 00:00:00

  • Substituted quinolines as noncovalent proteasome inhibitors.

    abstract::Screening of a library of diverse heterocyclic scaffolds identified substituted quinolines as inhibitors of the human proteasome. The heterocyclic library was prepared via a novel titanium-catalyzed multicomponent coupling reaction, which rendered a diverse set of isoxazoles, pyrimidines, pyrroles, pyrazoles and quino...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.04.005

    authors: McDaniel TJ,Lansdell TA,Dissanayake AA,Azevedo LM,Claes J,Odom AL,Tepe JJ

    更新日期:2016-06-01 00:00:00

  • Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists.

    abstract::Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.12.046

    authors: Xu R,Li S,Paruchova J,McBriar MD,Guzik H,Palani A,Clader JW,Cox K,Greenlee WJ,Hawes BE,Kowalski TJ,O'Neill K,Spar BD,Weig B,Weston DJ

    更新日期:2006-05-15 00:00:00

  • 4,4'-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity.

    abstract::Resveratrol (3,5,4'-trans-trihydroxystibene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidant activity. In order to find more active antioxidant with resveratrol as the lead compound we synthesized 4,4'-dihydroxy-trans-stilbene (4,4'-DHS)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.02.014

    authors: Fan GJ,Liu XD,Qian YP,Shang YJ,Li XZ,Dai F,Fang JG,Jin XL,Zhou B

    更新日期:2009-03-15 00:00:00

  • Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1).

    abstract::NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating α-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.10.006

    authors: Mayhoub AS,Marler L,Kondratyuk TP,Park EJ,Pezzuto JM,Cushman M

    更新日期:2012-12-15 00:00:00

  • Discovery of pyridine-based agrochemicals by using Intermediate Derivatization Methods.

    abstract::Pyridine-based compounds have been playing a crucial role as agrochemicals or pesticides including fungicides, insecticides/acaricides and herbicides, etc. Since most of the agrochemicals listed in the Pesticide Manual were discovered through screening programs that relied on trial-and-error testing and new agrochemic...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2015.09.031

    authors: Guan AY,Liu CL,Sun XF,Xie Y,Wang MA

    更新日期:2016-02-01 00:00:00

  • Design, synthesis and biological evaluation of novel 4-phenoxy-6,7-disubstituted quinolines possessing (thio)semicarbazones as c-Met kinase inhibitors.

    abstract::In continuing our efforts to identify small molecules able to inhibit c-Met kinase, three series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives (23a-w, 26a-d and 30a-d) bearing (thio)semicarbazone scaffold were designed, synthesized and evaluated for their cytotoxicity. The biological data revealed that mos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.02.003

    authors: Zhai X,Bao G,Wang L,Cheng M,Zhao M,Zhao S,Zhou H,Gong P

    更新日期:2016-03-15 00:00:00

  • Proteasome inhibition by new dual warhead containing peptido vinyl sulfonyl fluorides.

    abstract::The success of inhibition of the proteasome by formation of covalent bonds is a major victory over the long held-view that this would lead to binding the wrong targets and undoubtedly lead to toxicity. Great challenges are now found in uncovering ensembles of new moieties capable of forming long lasting ties. We have ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.05.042

    authors: Brouwer AJ,Herrero Álvarez N,Ciaffoni A,van de Langemheen H,Liskamp RM

    更新日期:2016-08-15 00:00:00

  • Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase.

    abstract::The purpose of the present study was to discover the extent of contribution to antityrosinase activity by adding hydroxy substituted benzoic acid, cinnamic acid and piperazine residues to vanillin. The study showed the transformation of vanillin into esters as shown in (4a-4d), (6a-6b), and (8a-8b). In addition, the r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.06.068

    authors: Ashraf Z,Rafiq M,Seo SY,Babar MM,Zaidi NU

    更新日期:2015-09-01 00:00:00

  • Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors.

    abstract::The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introductio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.12.056

    authors: Wan SB,Landis-Piwowar KR,Kuhn DJ,Chen D,Dou QP,Chan TH

    更新日期:2005-03-15 00:00:00

  • Synthesis and binding mode of heterocyclic analogues of suramin inhibiting the human basic fibroblast growth factor.

    abstract::The design, synthesis, and biological evaluation of a series of pyrrole and pyrazole congeners 2 of suramin, directed toward the development and identification of new ligands that complex the human fibroblast growth factor (bFGF), thereby inhibiting tumor-promoted angiogenesis, is reported. Compounds 2 were evaluated ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00052-2

    authors: Manetti F,Cappello V,Botta M,Corelli F,Mongelli N,Biasoli G,Borgia AL,Ciomei M

    更新日期:1998-07-01 00:00:00

  • Identification of new γ-hydroxybutenolides that preferentially inhibit the activity of mPGES-1.

    abstract::Microsomal prostaglandin E(2) synthase-1 (mPGES-1) has been recognized as novel, promising drug target for anti-inflammatory and anticancer drugs. mPGES-1 catalyzes the synthesis of the inducible prostaglandin E(2) in response to pro-inflammatory stimuli, rendering this enzyme extremely interesting in drug discovery p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.06.032

    authors: De Simone R,Bruno I,Riccio R,Stadler K,Bauer J,Schaible AM,Laufer S,Werz O

    更新日期:2012-08-15 00:00:00

  • Toward the development of chemoprevention agents (III): synthesis and anti-inflammatory activities of a new class of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes.

    abstract::A new series of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes were designed and synthesized. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Sixteen of these new compounds exhibited comparable or better anti-inflammatory activities than aspirin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.11.017

    authors: Bi L,Zhao M,Gu K,Wang C,Ju J,Peng S

    更新日期:2008-02-15 00:00:00

  • Discovery of novel 4-(2-fluorophenoxy)quinoline derivatives bearing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety as c-Met kinase inhibitors.

    abstract::A series of novel 4-(2-fluorophenoxy)quinoline derivatives containing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and six typical cancer cell lines (A549, H460, HT-29, MKN-45, U87MG and SMMC-7721). All the prepar...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.04.013

    authors: Li S,Zhao Y,Wang K,Gao Y,Han J,Cui B,Gong P

    更新日期:2013-06-01 00:00:00

  • New cannabinoid receptor antagonists as pharmacological tool.

    abstract::Synthesis and pharmacological evaluation of a new series of cannabinoid receptor antagonists of indazole ether derivatives have been performed. Pharmacological evaluation includes radioligand binding assays with [3H]-CP55940 for CB1 and CB2 receptors and functional activity for cannabinoid receptors on isolated tissue...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115672

    authors: González-Naranjo P,Pérez C,Girón R,Sánchez-Robles EM,Martín-Fontelles MI,Carrillo-López N,Martín-Vírgala J,Naves M,Campillo NE,Páez JA

    更新日期:2020-10-01 00:00:00

  • Switchable MRI contrast agents based on morphological changes of pH-responsive polymers.

    abstract::Magnetic resonance imaging (MRI) contrast agents are effective tools in both medical diagnosis and life science research. Various smart contrast agents have been developed for the visualization of biological phenomena. These contrast agents have molecular switches that increase or reduce MRI signal intensity in respon...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.005

    authors: Okada S,Mizukami S,Kikuchi K

    更新日期:2012-01-15 00:00:00

  • Synthesis and optical properties of pyrrolidinyl peptide nucleic acid bearing a base discriminating fluorescence nucleobase 8-(pyrene-1-yl)-ethynyladenine.

    abstract::A combination of fluorophore and nucleobase through a π-conjugated rigid linker integrates the base pairing and the fluorescence change into a single event. Such base discriminating fluorophore can change its fluorescence as a direct response to the base pairing event and therefore have advantages over tethered labels...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.10.008

    authors: Nim-Anussornkul D,Vilaivan T

    更新日期:2017-12-15 00:00:00

  • Cyclic voltammetric analysis of 2-styrylchromones: relationship with the antioxidant activity.

    abstract::2-Styrylchromones (2-SC) are a chemical family of oxygen heterocyclic compounds, vinylogues of flavones (2-phenylchromones), whose occurrence in nature has been reported. Recently, several 2-SC derivatives were demonstrated to have antioxidant properties, namely, xanthine oxidase inhibition, hepatoprotection against p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.072

    authors: Gomes A,Fernandes E,Garcia MB,Silva AM,Pinto DC,Santos CM,Cavaleiro JA,Lima JL

    更新日期:2008-09-01 00:00:00

  • Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.

    abstract::Chemical investigation of the organic extract obtained from the sponge Plakortis simplex collected in the South China Sea afforded five new polyketide endoperoxides (2 and 4-7), along with two known analogues (1 and 3). The stereostructures of these metabolites have been deduced on the basis of spectroscopic analysis ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.034

    authors: Chianese G,Persico M,Yang F,Lin HW,Guo YW,Basilico N,Parapini S,Taramelli D,Taglialatela-Scafati O,Fattorusso C

    更新日期:2014-09-01 00:00:00

  • Preparation of piperazine derivatives as 5-HT7 receptor antagonists.

    abstract::Twenty-four compounds of 4-methoxy-N-[3-(4-substituted phenyl-piperazine-1-yl)propyl] benzene sulfonamides and N-[3-(4-substituted phenyl-piperazine-1-yl)propyl] naphthyl sulfonamides were prepared and evaluated as 5-HT(7) receptor antagonists. Most of the compounds showed the IC(50) values of 12-580nM. Four methyl br...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.04.023

    authors: Yoon J,Yoo EA,Kim JY,Pae AN,Rhim H,Park WK,Kong JY,Park Choo HY

    更新日期:2008-05-15 00:00:00

  • Design, synthesis, conformational analysis, and biological studies of urotensin-II lactam analogues.

    abstract::Human urotensin II (hU-II; H-Glu-Thr-Pro-Asp-cyclo[Cys-Phe-Trp-Lys-Tyr-Cys]-Val-OH) is a disulfide bridged undecapeptide recently identified as the ligand of an orphan G protein-coupled receptor. hU-II has been described as the most potent vasoconstrictor compound identified to date. With the aim of replacing the disu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00372-3

    authors: Grieco P,Carotenuto A,Patacchini R,Maggi CA,Novellino E,Rovero P

    更新日期:2002-12-01 00:00:00

  • Searching for novel N1-substituted benzimidazol-2-ones as non-nucleoside HIV-1 RT inhibitors.

    abstract::Non-nucleoside reverse transcriptase inhibitors (NNRTIs) represent an integral part of the currently available combination antiretroviral therapy (cART) contributing to reduce the AIDS-mortality and turned the disease from lethal to chronic. In this context we recently reported a series of 6-chloro-1-(3-methylphenylsu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.05.040

    authors: Ferro S,Buemi MR,De Luca L,Agharbaoui FE,Pannecouque C,Monforte AM

    更新日期:2017-07-15 00:00:00

  • Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA.

    abstract::A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure-activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demons...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.04.009

    authors: Wynn JE,Zhang W,Tebit DM,Gray LR,Hammarskjold ML,Rekosh D,Santos WL

    更新日期:2016-09-01 00:00:00

  • Hippuryl-alpha-methylphenylalanine and hippuryl-alpha-methylphenyllactic acid as substrates for carboxypeptidase A. Syntheses, kinetic evaluation and mechanistic implication.

    abstract::(R)- and (S)-Hippuryl-alpha-methylphenylalanine [(R)- and (S)-Hipp-alpha-MePhe] and (S)-hippuryl-alpha-methylphenyllactic acid [(S)-Hipp-alpha-MeOPhe] were synthesized and evaluated as substrates for carboxypeptidase A (CPA) in an effort to shed further light on the catalytic mechanism of the enzyme. The rate of CPA-c...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00006-7

    authors: Lee M,Kim DH

    更新日期:2000-04-01 00:00:00

  • Novel iron complexes bearing N6-substituted adenosine derivatives: synthesis, magnetic, 57Fe Mössbauer, DFT, and in vitro cytotoxicity studies.

    abstract::Iron complexes (1-7) involving N6-benzyladenosine derivatives of the predominant composition [Fe(L(n))Cl(3)].H(2)O {where L(1)=N6-(2-fluorobenzyl)adenosine (1), L(2)=N6-(4-fluorobenzyl)adenosine (2), L(3)=N6-(2-trifluoromethylbenzyl)adenosine (3), L(4)=N6-(3-trifluoromethylbenzyl)adenosine (4), L(5)=N6-(4-trifluoromet...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.082

    authors: Trávnícek Z,Mikulík J,Cajan M,Zboril R,Popa I

    更新日期:2008-09-15 00:00:00

  • Advances in inhibition of protein-protein interactions targeting hypoxia-inducible factor-1 for cancer therapy.

    abstract::Hypoxia is a common characteristic of many types of solid tumors and is associated with tumor propagation, malignant progression, and resistance to anti-cancer therapy. HIF-1 pathway is one of the survival pathways activated in tumor in response to hypoxia. In hypoxic condition, hypoxia-inducible factor-1α (HIF-1α) is...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2019.01.042

    authors: Li J,Xi W,Li X,Sun H,Li Y

    更新日期:2019-04-01 00:00:00

  • Synthesis and biological activity of semipeptoid farnesyltransferase inhibitors.

    abstract::Semipeptoids derived from the Ras farnesyl transferase inhibitor, CVFM, were synthesized by the Simultaneous Multiple Analogue Peptide Synthesis methodology. The semipeptoids were screened for their in vitro inhibition potency towards farnesyl transferase and geranylgeranyl transferase. Structure-activity relationship...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(96)00197-6

    authors: Reuveni H,Gitler A,Poradosu E,Gilon C,Levitzki A

    更新日期:1997-01-01 00:00:00

  • Synthesis and structure-activity relationships of dual histamine H2 and gastrin receptor antagonists with decreased hydrophobicity.

    abstract::In order to study structure-activity relationships of the previously reported dual histamine H2 and gastrin receptor antagonists and also to improve their low oral absorbability, we tried two chemical modifications. One tried to decrease the high hydrophobicity of the parent hybrid compounds to an appropriate level by...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)00074-6

    authors: Kawanishi Y,Ishihara S,Tsushima T,Hagishita S,Ishikawa M,Ishihara Y

    更新日期:1997-07-01 00:00:00