Sesquiterpenes from Ainsliaea fragrans and their inhibitory activities against cyclooxygenases-1 and 2.

Abstract:

:One new guaiane-type sesquiterpene glycoside, 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (1), was isolated from the whole herb of Ainsliaea fragrans (Compositae), together with five known sesquiterpene lactones: 8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (2), 8alpha-hydroxy-11alpha,13-dihydrozaluzanin C (3), 3alpha-hydroxy-11beta,13-dihydro-8alpha-O-beta-D-glucozaluzanin C (4), 3beta-hydroxy-11beta,13-dihydro-8alpha-O-beta-D-glucozaluzanin C (5), 3beta-O-beta-D-glucozaluzanin C (6). The structures of isolated compounds were established by means of 1D and 2D NMR spectroscopy and chemical methods. All isolates obtained in the present study were evaluated for their inhibitory effects against cyclooxygenases-1 and 2 in vitro, and the structure-activity relationships were also discussed.

authors

Wang H,Wu T,Yan M,Liu G,Li P,Zhang XQ,Ye WC,Zhang LY

doi

10.1248/cpb.57.597

subject

Has Abstract

pub_date

2009-06-01 00:00:00

pages

597-9

issue

6

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/57.597

journal_volume

57

pub_type

杂志文章
  • Synthesis and anti-HIV-1 activity of new delavirdine analogues carrying arylpyrrole moieties.

    abstract::In our search for novel anti-human immunodeficiency virus (HIV)-1 agents, 14 delavirdine analogues were synthesized and evaluated as potential anti-HIV-1 agents in cell-based assays. Compound 1Aa exhibited potent and selective anti-HIV-1 activity in acutely infected MT4 cells, with effective concentration (EC50) value...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1406

    authors: Pinna GA,Loriga G,Murineddu G,Grella G,Mura M,Vargiu L,Murgioni C,La Colla P

    更新日期:2001-11-01 00:00:00

  • Simultaneous determination of triterpene saponins in ginseng drugs by high-performance liquid chromatography.

    abstract::A HPLC method for the simultaneous determination of 11 triterpene saponins with four-type aglycones (protopanaxadiol, protopanaxatriol, ocotillol and oleanolic acid types) in Ginseng drugs was developed and validated. Using a gradient of acetonitrile and 10 mM K-phosphate buffer (pH 5.80) as the mobile phase and UV de...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.995

    authors: Zhu S,Zou K,Cai S,Meselhy MR,Komatsu K

    更新日期:2004-08-01 00:00:00

  • Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa.

    abstract::Three new hydrolyzable tannins, euphormisins M1, M2, and M3, were isolated from Euphorbia humifusa WILLD., and respectively characterized as 1,3,6-tri-O-galloyl-4-O- brevifolincarboxyl-beta-D-glucose (19), an oxidative metabolite (23) of geraniin, and 1,3,6-tri-O-galloyl-alpha-D-glucose (18), by spectroscopic and chem...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1803

    authors: Yoshida T,Amakura Y,Liu YZ,Okuda T

    更新日期:1994-09-01 00:00:00

  • Cardenolides from Antiaris toxicaria as potent selective Nur77 modulators.

    abstract::Toxicarioside D (1), a new cardenolide, along with 10 other known ones, was isolated from the stem of Antiaris toxicaria LESCH. by bioassay-guided fractionation. Their structures were determined on the basis of spectroscopic analysis. All the reported compounds effectively inhibited the growth of various cancer cell l...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1005

    authors: Jiang MM,Dai Y,Gao H,Zhang X,Wang GH,He JY,Hu QY,Zeng JZ,Zhang XK,Yao XS

    更新日期:2008-07-01 00:00:00

  • Prolonged Distribution of Tranilast in the Eyes after Topical Application onto Eyelid Skin.

    abstract::Tranilast, a lipophilic drug with various ophthalmic applications, was used as a model drug to establish the possibility of delivering lipophilic drugs through the eyelid skin. Pharmacokinetics and tissue distribution studies were conducted employing three application methods (topical application onto eyelid skin, eye...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00289

    authors: See GL,Arce F Jr,Itakura S,Todo H,Sugibayashi K

    更新日期:2020-01-01 00:00:00

  • Detection and identification of loline and its analogues in horse urine.

    abstract::Several kinds of loline-type alkaloids, norloline, loline, N-acetylnorloline, N-acetylloline, N-formylnorloline, N-formylloline and N-methylloline were detected in the urine of race-horses. Furthermore, a new compound of the alkaloids, N-senecioylnorloline, was also found and identified. These compounds were mainly id...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.964

    authors: Takeda A,Suzuki E,Kamei K,Nakata H

    更新日期:1991-04-01 00:00:00

  • Oxidative Stress Is Involved in the Renal Dysfunction Induced by Sinoaortic Denervation in Rats.

    abstract::The hypothesis that oxidative stress contributes to renal dysfunction in sinoaortically denervated (SAD) rats was investigated. Rats were sinoaortically denervated and received treatment with tempol (0.5 mmol/L in drinking water) for 8 weeks. Although the tempol treatment of the SAD rats had no significant effect on b...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00318

    authors: Sun Y,Fan J,Chai D,Zhang M

    更新日期:2016-10-01 00:00:00

  • Molecular geometry and physiochemical characteristics of selected anilinoquinolines, indolo[3,2-c]quinolines and tetrahydroindolo[3,2-d]benzazepines.

    abstract::The molecular geometry, acid dissociation constants and partition coefficients of the anilinoquinoline (I), indolo[3,2-c]quinoline (II) and tetrahydroindolo[3,2-d] [1]benzazepine (III) ring systems have been determined using representative compounds: 7-chloro-4-(p-anisidino)quinoline (Ia), 3-chloro-8-methoxy-11H-indol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1084

    authors: Koh HL,Go ML,Ngiam TL

    更新日期:1994-05-01 00:00:00

  • Immobilized triazine-type dehydrocondensing reagents for carboxamide formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl.

    abstract::New triazine-type dehydrocondensing reagents, such as ROMP-Trz-Cl and ROMP(OH)-Trz-Cl, were synthesized by a ring opening metathesis polymerization (ROMP) method, and these showed higher loading than conventional polymer-supported condensing reagents. These polymers effect the formation of amides in good yields by add...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.825

    authors: Hioki K,Kameyama S,Tani S,Kunishima M

    更新日期:2007-05-01 00:00:00

  • Cytotoxic bisnor- and norditerpene dilactones having 7alpha,8alpha-epoxy-9,11-enolide substructure from Podocarpus macrophyllus D. DON.

    abstract::Fourteen new bisnor- and norditerpene dilactones, makilactones E-R, having a 7alpha : 8alpha-epoxy-9,11-enolide substructure, were isolated from a methanolic extract of the root and the bark of Podocarpus macrophyllus D. DON (Podocarpaceae) with thirteen known bisnor- and norditerpenoids, and the structures of those n...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.668

    authors: Sato K,Inaba Y,Park HS,Akiyama T,Koyama T,Fukaya H,Aoyagi Y,Takeya K

    更新日期:2009-07-01 00:00:00

  • Development of new cycloaddition reactions based on the unique reactivity of unsaturated hydrocarbons.

    abstract::We discovered that the reactivity of some conjugated and electron-deficient hydrocarbons was quite different in the presence of transition metal catalysts. In this review we report our development and applications of the highly selective palladium and nickel-catalyzed cycloaddition reactions of unsaturated hydrocarbon...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.53.1069

    authors: Saito S

    更新日期:2005-09-01 00:00:00

  • Diarylureas and diarylamides with pyrrolo[2,3-d]pyrimidine scaffold as broad-spectrum anticancer agents.

    abstract::A series of diarylureas and diarylamides possessing pyrrolo[2,3-d]pyrimidine scaffold was designed and synthesized. The in vitro antiproliferative activities of a selected group of the target compounds against NCI-60 cell line panel were tested and compared with Sorafenib and Imatinib as reference compounds. Most of t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00249

    authors: El-Gamal MI,Oh CH

    更新日期:2014-01-01 00:00:00

  • Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis.

    abstract::Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1285

    authors: Thanigaimalai P,Lee KC,Sharma VK,Sharma N,Roh E,Kim Y,Jung SH

    更新日期:2011-01-01 00:00:00

  • Schisandrosides A-D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of Schisandra chinensis.

    abstract::Four new dibenzocyclooctadiene lignan glucosides, schisandrosides A-D (1-4), as well as two known rare nortriterpenoids, micrandilactone C (5) and propindilactone Q (6), were isolated from the roots of Schisandra chinensis BAILLON (Schisandraceae). The structure of compounds 1-4 were elucidated by physical and spectro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00400

    authors: Kim HM,Ryu B,Lee JS,Choi JH,Jang DS

    更新日期:2015-01-01 00:00:00

  • Studies on antiulcer drugs. V. Synthesis and antiulcer activity of aralkylbenzazoles.

    abstract::A series of 2-alkylamino-5- or 6-aralkyl-substituted benzazoles were synthesized and tested for histamine H2-receptor antagonist and anti-stress ulcer activities. These new compounds showed little or no histamine H2-receptor antagonist activity in contrast to imidazo[1,2-a]pyridine analogues (I). On antiulcer assay, h...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2062

    authors: Katsura Y,Inoue Y,Tomoi M,Takasugi H

    更新日期:1992-08-01 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

  • Absolute Structures of Wedelolide Derivatives and Structure-Activity Relationships of Protein Tyrosine Phosphatase 1B Inhibitory ent-Kaurene Diterpenes from Aerial Parts of Wedelia spp. Collected in Indonesia and Japan.

    abstract::Two sesquiterpene lactones with the (9R)-eudesman-9,12-olide framework, wedelolides I and J, have been isolated together with five eudesmanolide sesquiterpenes and twelve ent-kaurene diterpenes from the aerial parts of Indonesian Wedelia prostrata. The absolute configurations of wedelolides I and J, proposed in the pr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00117

    authors: Abdjul DB,Yamazaki H,Kanno SI,Kirikoshi R,Tomizawa A,Takahashi O,Maarisit W,Losung F,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Namikoshi M

    更新日期:2018-01-01 00:00:00

  • Biotransformation of chrysin and apigenin by Cunninghamella elegans.

    abstract::Biotransformation of chrysin by Cunninghamella elegans NRRL 1392 produced apigenin, apigenin 7-sulfate, apigenin 7,4'-disulfate, and a new metabolite identified as chrysin 7-sulfate. On the other hand, fermentation of apigenin, using the same microorganism, yielded apigenin 7-sulfate and apigenin 7,4'-disulfate. The s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.671

    authors: Ibrahim AR

    更新日期:2005-06-01 00:00:00

  • Modeling the entrainer effects on solubility of solutes in supercritical carbon dioxide.

    abstract::Applicability of a previously published equation for calculating the solubility of solutes in supercritical carbon dioxide was extended to calculate the solubility in entrained supercritical carbon dioxide employing 42 experimental data sets collected from the literature. The accuracy of the proposed model was evaluat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.290

    authors: Jouyban A,Khoubnasabjafari M,Chan HK

    更新日期:2005-03-01 00:00:00

  • Novel 4-phenoxy-2-(1-piperazinyl)quinazolines as potent anticonvulsive and antihypoxic agents.

    abstract::A series of 4-phenoxy-2-(1-piperazinyl)quinazolines was synthesized and examined for anticonvulsive and antihypoxic activities. Many of the compounds exhibited potent anticonvulsive activity comparable to that of carbamazepine or phenytoin. Among them, 4-phenoxy-2-(4-propyl-1-piperazinyl)quinazoline (5w) was selected ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.681

    authors: Hori M,Iemura R,Hara H,Ozaki A,Sukamoto T,Ohtaka H

    更新日期:1990-03-01 00:00:00

  • Abietane diterpenoids from the barks of Cryptomeria japonica.

    abstract::From the bark of Cryptomeria japonica were isolated sugikurojins I (1) and J (2), and an abietane derivative (3) was obtained for the first time as a natural product. These structures were elucidated primarily through extensive NMR experiments. Sugikurojin I (1) has a unique skeleton incorporating an abietane diterpen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.574

    authors: Yoshikawa K,Suzuki K,Umeyama A,Arihara S

    更新日期:2006-04-01 00:00:00

  • Intercalation compound of diclofenac sodium with layered inorganic compounds as a new drug material.

    abstract::The intercalation reaction of diclofenac sodium (DFS) with layered inorganic compounds, gamma-titanium phosphate (gamma-TiP), proton type titanium oxide (H-TiO2) and sodium type synthetic mica (Na-TSM), was examined on. The direct reaction of DFS in ethanol-water mixed solvent resulted in the large amount accommodatio...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1396

    authors: Tajima T,Suzuki N,Watanabe Y,Kanzaki Y

    更新日期:2005-11-01 00:00:00

  • Separation of sympathomimetic amines of abuse and related compounds by micellar electrokinetic chromatography.

    abstract::Separation of twelve sympathomimetic amines and related compounds by micellar electrokinetic chromatography (MEKC) with UV absorbance detection is described. These amines were well separated within 25 min using 50 mM sodium tetraborate solution containing 15 mM sodium dodecylsulfate (SDS) of pH 9.3 as a running soluti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.905

    authors: Kuroda N,Sato D,Ohyama K,Wada M,Nakahara Y,Nakashima K

    更新日期:2001-07-01 00:00:00

  • Development and validation of a sensitive GC-MS method for the determination of alkylating agent, 4-chloro-1-butanol, in active pharmaceutical ingredients.

    abstract::The analysis of genotoxic impurities (GTIs) in active pharmaceutical ingredients (APIs) is a challenging task. The target detection limit (DL) in an API is typically around 1 ppm (1 µg/g API). Therefore, a sensitive and selective analytical method is required for their analysis. 4-Chloro-1-butanol, an alkylating agent...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00916

    authors: Harigaya K,Yamada H,Yaku K,Nishi H,Haginaka J

    更新日期:2014-01-01 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

  • Effects of dehydration temperatures on moisture absorption and dissolution behavior of theophylline.

    abstract::Anhydrous theophylline was prepared by heating theophylline monohydrate at temperatures between 60 degrees C and 140 degrees C. The effects of dehydration temperatures on the moisture absorption and dissolution behavior of anhydrous theophylline were investigated in this study. The hydration rate of anhydrous theophyl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1526

    authors: Ono M,Tozuka Y,Oguchi T,Yamamoto K

    更新日期:2001-12-01 00:00:00

  • Conferols A and B, new anti-inflammatory 4-hydroxyisoflavones from Caragana conferta.

    abstract::Conferols A (1) and B (2), the new 4-hydroxyisoflavones, have been isolated from the dichloromethane sub-fraction of the methanolic extract of Caragana conferta along with 3',5'-dihydroxy, 7,4'-dimethoxyisoflavone (3), E-cinnamic acid (4), tetracosyl 3,4-dihydroxy-E-cinnamate (5), docosyl 3,4-dihydroxy-E-cinnamate (6)...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.415

    authors: Khan R,Malik A,Adhikari A,Qadir MI,Choudhary MI

    更新日期:2009-04-01 00:00:00

  • Fasciculic acids A, B and C as calmodulin antagonists from the mushroom Naematoloma fasciculare.

    abstract::Three new fasciculol esters, fasciculic acids A (1), B (2) and C (3), having potent calmodulin antagonistic activity were isolated from the toxic mushroom Naematoloma fasciculare (Fr.) Karst. Their structures were elucidated on the basis of spectral and chemical evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3247

    authors: Takahashi A,Kusano G,Ohta T,Ohizumi Y,Nozoe S

    更新日期:1989-12-01 00:00:00

  • 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.

    abstract::From the air-dried roots of Glycyrrhiza uralensis Fischer collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named isoliquiritin apioside were isolated together with glycyrrhizin, 18 alpha-glycyr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1567

    authors: Kitagawa I,Hori K,Uchida E,Chen WZ,Yoshikawa M,Ren J

    更新日期:1993-09-01 00:00:00

  • Two new lignans from the stem bark of Magnolia obovata and their cytotoxic activity.

    abstract::Two new lignans, 4-methoxymagnaldehyde B (1) and coumanolignan (2), were isolated from the stem bark of Magnolia obovata, together with 11 known compounds (3-13). The structures of compounds 1 and 2 were determined to be 5'-allyl-2'-hydroxyphenyl-4-methoxy-3-cinnamic aldehyde (1) and 6-allyl-8-(5'-allyl-2'-hydroxyphen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.115

    authors: Youn U,Chen QC,Lee IS,Kim H,Yoo JK,Lee J,Na M,Min BS,Bae K

    更新日期:2008-01-01 00:00:00