COX-1, COX-2 inhibitors and antifungal agents from Croton hutchinsonianus.

Abstract:

:Two new compounds, 3'-(4''-hydroxy-3'',5''-dimethoxyphenyl)-propyl benzoate (1) and 3'-(4''-hydroxyphenyl)-propyl benzoate (3) together with known compounds, 3'-(4''-hydroxy-3''-methoxyphenyl)-propyl benzoate (2), poilaneic acid (4), farnesyl acetone (5) and 4-hydroxybenzaldehyde (6) were isolated and identified from the branches of Croton hutchinsonianus. Their structures were determined by spectroscopic methods. The three phenylpropyl benzoates (1-3) were found to exhibit antifungal activity against Candida albicans (IC(50) 5.36-11.41 microg/ml). Compounds 1-2 (IC(50) 2.11-4.95 microg/ml) exhibited potent but non-selective activity against the enzymes cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) whereas 3 (IC(50) 1.88 microg/ml) preferentially inhibited the enzyme COX-2.

authors

Athikomkulchai S,Prawat H,Thasana N,Ruangrungsi N,Ruchirawat S

doi

10.1248/cpb.54.262

subject

Has Abstract

pub_date

2006-02-01 00:00:00

pages

262-4

issue

2

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/54.262

journal_volume

54

pub_type

杂志文章
  • QSAR studies on chalcones and flavonoids as anti-tuberculosis agents using genetic function approximation (GFA) method.

    abstract::Design of compounds having good anti-tubercular activity is gaining much importance in the field of tuberculosis research due to reemergence of antibiotic resistance strains. In this paper quantitative structure activity relationships (QSAR) were developed on chalcones, chalcone-like compounds, flavones and flavanones...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.44

    authors: Sivakumar PM,Geetha Babu SK,Mukesh D

    更新日期:2007-01-01 00:00:00

  • New fatty monoesters of erythromycin A.

    abstract::New fatty polyenic (linoleic, linolenic, arachidonic, linoelaidic) mono esters of erythromycin A have been synthesized by using various reagents such as acyl chloride, carboxylic acid anhydride, and mixed carbonic anhydride. These different ways of activating the fatty acid allowed a regioselectivity of esterification...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1672

    authors: Philippe M,Campos A,Sebag H,Rougier A,Dupuis D,Saint-Leger D,Vanlerberghe G

    更新日期:1990-06-01 00:00:00

  • 2-Acyl-tetrahydroisoquinoline-3-carboxylic acids: lead compounds with triple actions, peroxisome proliferator-activated receptor α/γ agonist and protein-tyrosine phosphatase 1B inhibitory activities.

    abstract::2-Acyl-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and biologically evaluated. (S)-2-(2,4-Hexadienoyl)-7-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (14) showed peroxisome proliferator-activated receptor γ (PPARγ) and PPARα agonist activities and ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.876

    authors: Otake K,Azukizawa S,Takahashi K,Fukui M,Shibabayashi M,Kamemoto H,Kasai M,Shirahase H

    更新日期:2011-01-01 00:00:00

  • Triterpenoids from Camellia japonica and their cytotoxic activity.

    abstract::From the ethyl acetate fraction of the stem bark of Camellia japonica, three new triterpenoids, 3beta-O-acetyl-16beta-hydroxy-12-oxoolean (6), 3beta-O-acetyl-16beta-hydroxy-11-oxoolean-12-ene (7), and 3beta-O-acetyl-16beta-hydroxyolean-12-ene (8), along with seven known compounds, 3alpha-hydroxy-1-oxofriedelan (1), fr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.121

    authors: Thao NT,Hung TM,Lee MK,Kim JC,Min BS,Bae K

    更新日期:2010-01-01 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

  • New triterpenoids from the stem barks of Drypetes tessmanniana.

    abstract::The MeOH extract of the stem barks of Drypetes tessmanniana (Euphorbiaceae) afforded two new triterpene derivatives characterized as 3beta-O-(E)-3,5-dihydroxycinnamoyl-11-oxo-olean-12-ene and 3beta,6alpha-dihydroxylup-20(29)-ene together with seven known compounds. Their structures were established on the basis of spe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1321

    authors: Dongfack MD,Van-Dufat HT,Lallemand MC,Wansi JD,Seguin E,Tillequin F,Wandji J

    更新日期:2008-09-01 00:00:00

  • Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor.

    abstract::An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a-g and the intermediate diols 4a-g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vit...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.270

    authors: Zhang P,Yang Y,Zheng X,Huang W,Ma Z,Shen Z

    更新日期:2012-01-01 00:00:00

  • A new stilbene with tyrosinase inhibitory activity from Chlorophora excelsa.

    abstract::A new stilbene, 4-[(2"E)-7"-hydroxy-3",7"-dimethyloct-2"-enyl]-2',3,4',5-tetrahydroxy-trans-stilbene (1), and the known compound chlorophorin (2) were isolated from the heartwood of Chlorophora excelsa. Both 1 and 2 showed tyrosinase inhibitory activity with IC(50) values of 96 and 1.3 microM, respectively. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.318

    authors: Shimizu K,Yasutake S,Kondo R

    更新日期:2003-03-01 00:00:00

  • Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.

    abstract::Analogs related to 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D3 (ED-71) (4), oxa-type and carba-type analogs of vitamin D3 bearing substituents at the 2 beta-position of 1 alpha,25-dihydroxyvitamin D3 (1), were synthesized from the alpha-epoxides (6 and 13). Three analogs, ED-71 (4) and two carba-type anal...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1626

    authors: Ono Y,Watanabe H,Shiraishi A,Takeda S,Higuchi Y,Sato K,Tsugawa N,Okano T,Kobayashi T,Kubodera N

    更新日期:1997-10-01 00:00:00

  • Tryptanthrin-loaded nanoparticles for delivery into cultured human breast cancer cells, MCF7: the effects of solid lipid/liquid lipid ratios in the inner core.

    abstract::Tryptanthrin is an ancient medicine which recently was also found to have a function of downregulating multidrug resistance (MDR). However, tryptanthrin is insoluble in water, which limits its availability for delivery into cancer cells. There is a need to improve delivery systems to increase the inhibition of MDR. Th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.266

    authors: Fang YP,Lin YK,Su YH,Fang JY

    更新日期:2011-01-01 00:00:00

  • Importance of Proton-Coupled Electron Transfer from Natural Phenolic Compounds in Superoxide Scavenging.

    abstract::The superoxide O2(·-) scavenging reaction of (+)-catechin (Cat), quercetin (Que), rutin, and α-tocopherol (α-TOH) as natural phenolic compounds is investigated on the basis of electrochemical and ESR spectral measurements with the aid of density functional theory (DFT) calculations. Reversibility of the O2/O2(·-) redo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00447

    authors: Nakayama T,Uno B

    更新日期:2015-01-01 00:00:00

  • New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Uña de Gato" (Uncaria tomentosa).

    abstract::A new oleanan-type triterpene and three new cincholic acid glycosides were isolated from Peruvian "Una de Gato" (Cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1258

    authors: Kitajima M,Hashimoto K,Sandoval M,Aimi N,Takayama H

    更新日期:2004-10-01 00:00:00

  • Structure-Activity Relationship Study on Col-003, a Protein-Protein Interaction Inhibitor between Collagen and Hsp47.

    abstract::This study demonstrates the structure-activity relationship of Col-003, a potent collagen-heat-shock protein 47 (Hsp47) interaction inhibitor. Col-003 analogues were successfully synthesized by Pd(0)-catalyzed cross-coupling reactions of 5-bromosalicylaldehyde derivatives with alkyl-metal species, and the inhibitory a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00634

    authors: Yoshida M,Saito M,Ito S,Ogawa K,Goshima N,Nagata K,Doi T

    更新日期:2020-03-01 00:00:00

  • Oxygenated hexylitaconates from a marine sponge-derived fungus Penicillium sp.

    abstract::In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as α,β-dicarboxylic acid d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.120

    authors: Li JL,Zhang P,Lee YM,Hong J,Yoo ES,Bae KS,Jung JH

    更新日期:2011-01-01 00:00:00

  • Pharmacokinetics of isofraxidin in rat plasma after oral administration of the extract of Acanthopanax senticosus using HPLC with solid phase extraction method.

    abstract::High-performance liquid chromatography coupled with solid phase extraction method was developed for determination of isofraxidin in rat plasma after oral administration of Acanthopanax senticosus extract (ASE), and pharmacokinetic parameters of isofraxidin either in ASE or pure compound were measured. The HPLC analysi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1291

    authors: Sun H,Lv H,Zhang Y,Wang X,Bi K,Cao H

    更新日期:2007-09-01 00:00:00

  • Green and efficient synthesis of quinoxaline derivatives via ceric ammonium nitrate promoted and in situ aerobic oxidation of alpha-hydroxy ketones and alpha-keto oximes in aqueous media.

    abstract::The direct conversion of alpha-hydroxy ketones and alpha-keto oximes into quinoxaline derivatives in the presence of a catalytic amount of ceric ammonium nitrate via metal-catalyzed aerobic oxidation followed by in situ trapping with aromatic 1,2-diamines in water as a green and efficient reaction media, is reported. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.79

    authors: Shaabani A,Maleki A

    更新日期:2008-01-01 00:00:00

  • A novel fluorescent probe for zinc ion based on boron dipyrromethene (BODIPY) chromophore.

    abstract::ZnAB has the combined structure of N,N-bis(2-pyridylmethyl)ethylenediamine as a specific chelater for Zn(2+) and 1,3,5,7-tetramethyl-8-phenyl-boron dipyrromethene as a fluorophore. Complexation of ZnAB with Zn(2+) produces a remarkable enhancement of fluorescence intensity. ZnAB has the advantages of less sensitivity ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.700

    authors: Koutaka H,Kosuge J,Fukasaku N,Hirano T,Kikuchi K,Urano Y,Kojima H,Nagano T

    更新日期:2004-06-01 00:00:00

  • Multiple solubility maxima of oxolinic acid in mixed solvents and a new extension of Hildebrand solubility approach.

    abstract::A new extension of the Hildebrand solubility approach which describes drug solubility in solvent mixtures showing multiple solubility peaks, the chameleonic effect, is proposed. The experimental solubilities of oxolinic acid were measured at 25 degrees C in solvent mixtures of ethanol-water and ethanol-ethyl acetate. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.175

    authors: Jouyban-Gharamaleki A,Romero S,Bustamante P,Clark BJ

    更新日期:2000-02-01 00:00:00

  • Design, synthesis, and cytotoxic activity of Michael acceptors and enol esters in the benzo[b]acronycine series.

    abstract::A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4-6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (+/-)-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.919

    authors: Doan Thi Mai H,Gaslonde T,Michel S,Koch M,Tillequin F,Bailly C,David-Cordonnier MH,Pfeiffer B,Léonce S,Pierré A

    更新日期:2005-08-01 00:00:00

  • The average unwinding angle of DNA duplex produced by the binding of chromomycin A3.

    abstract::The effect of chromomycin A3 binding on the geometry of DNA duplex (plasmid pBR322) has been examined using topoisomerase I relaxation followed by gel electrophoresis. To determine the equilibrium constant of this drug-DNA binding-dissociation reaction in the same concentration range (ca. 10(-5) M) in the same buffer ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1667

    authors: Utsuno K,Kojima K,Maeda Y,Tsuboi M

    更新日期:1998-11-01 00:00:00

  • In-die evaluation of capping tendency of pharmaceutical tablets using force-displacement curve and stress relaxation parameter.

    abstract::A novel in-die evaluation method of tablet capping tendency was proposed based on a force-displacement curve and stress relaxation parameter in a tableting process. In our previous study (Chem. Pharm. Bull., 59, 2011, Nakamura et al.), the phase diagram consisting of elastic recovery energy (E(e)) and plastic deformat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.772

    authors: Nakamura H,Sugino Y,Watano S

    更新日期:2012-01-01 00:00:00

  • Contribution of prostaglandins to the renal responses to magnesium lithospermate B isolated from salviae miltiorrhizae radix.

    abstract::The involvement of prostanoids in the improvement of adenine-induced renal failure in rats by magnesium lithospermate B was studied. After intraperitoneal administration of magnesium lithospermate B to renal failure rats, the levels of glomerular filtration rate, renal plasma flow and renal blood flow were increased. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1568

    authors: Yokozawa T,Chung HY,Lee TW,Oura H,Tanaka T,Nonaka G,Nishioka I,Hirai A

    更新日期:1989-06-01 00:00:00

  • Synthesis and antifungal activity of novel 14-membered benzomacrolides, as galbonolide analogues.

    abstract::Asymmetric total synthesis of benzene analogues of galbonolide, a 14-membered antifungal macrolide, possessing a benzene ring instead of a conjugated diene structure, was achieved starting from chiral 1-aryl-1-propanol obtained by enzyme-catalyzed kinetic resolution with high enantioselectivity. Representatively, a me...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.163

    authors: Sakoh H,Sakuraba S,Sugimoto Y,Imamura H,Jona H,Yamada K,Bamba-Nagano R,Hashizume T,Morishima H

    更新日期:2004-01-01 00:00:00

  • Immediate release tablets of telmisartan using superdisintegrant-formulation, evaluation and stability studies.

    abstract::Telmisartan (anti-hypertensive) is insoluble in water; hence the drug may be slowly or incompletely dissolved in the gastro intestinal tract. So the rate of dissolution and therefore its bioavailability is less (bioavailability 42%). In the present study an attempt has been made to prepare immediate release tablets of...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.575

    authors: Sekar V,Chellan VR

    更新日期:2008-04-01 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

  • Synthesis and evaluation of (piperidinomethylene)bis(phosphonic acid) derivatives as anti-osteoporosis agents.

    abstract::Some (piperidinomethylene)bis(phosphonic acid) derivatives were prepared and their activity to inhibit a rise in serum calcium induced by parathyroid hormone in thyroparathyroidectomised rats was evaluated. Several (4-alkylidene-, 4,4-dialkyl-, or 4-alkyl-4-halopiperidinomethylene)bis(phosphonic acid) derivatives show...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1971

    authors: Mimura M,Hayashida M,Nomiyama K,Ikegami S,Iida Y,Tamura M,Hiyama Y,Ohishi Y

    更新日期:1993-11-01 00:00:00

  • Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method.

    abstract::The hydrolysis of protopanaxadiol-type saponin mixture by various glycoside hydrolases was examined. Among these enzymes, crude preparations of lactase from Aspergillus oryzae, beta-galactosidase from A. oryzae, and cellulase from Trichoderma viride were found to produce ginsenoside F(2) [3-O-(beta-D-glucopyranosyl)-2...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1522

    authors: Ko SR,Suzuki Y,Suzuki K,Choi KJ,Cho BG

    更新日期:2007-10-01 00:00:00

  • Reductive dimerization of alkylidenemalonates using samarium(II) diiodide and 1H-NMR behavior of the dimers, 2,3-diaryl-1,1,4,4-butanetetracarboxylates.

    abstract::Alkylidenemalonates were readily dimerized in the presence of SmI2 to give 2,3-disubstituted 1,1,4,4-butanetetracarboxylates as mixtures of meso and racemic isomers in moderate to good yields. The structure of the less polar isomer of tetraethyl 2,3-diphenyl-1,1,4,4-butanetetracarboxylate was determined by X-ray cryst...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1799

    authors: Yamashita M,Okuyama K,Kawasaki I,Nakamura S,Nagamine R,Tsujita T,Ohta S

    更新日期:2000-11-01 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

  • MRI Monitoring of the Mixed State of Admixtures Consisting of Moisturizing Cream and Steroid Ointment during the Mixing Process by a Revolution/Rotation-Type Hybrid Mixer.

    abstract::The admixture of a steroid ointment and a moisturizing cream is frequently prescribed to patients suffering from atopic dermatitis. For the mixing operation, a revolution/rotation-type hybrid mixer is widely used in pharmacy. The purpose of this study was to monitor the mixed state of the admixtures during the mixing ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00490

    authors: Yokokawa M,Setoyama H,Okada K,Hayashi Y,Machida Y,Onuki Y,Obata Y

    更新日期:2018-01-01 00:00:00