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 elucidated on the basis of extensive spectroscopic experiments, mainly one and two dimensional (1D- and 2D)-NMR, and the absolute configuration of 5 was determined by the measurement of specific rotation. The isolated compounds were evaluated for their protein tyrosine phosphatase-1B (PTP1B) inhibitory activity. The results showed that compounds 5-7 exhibited more potent PTP1B inhibitory effects with IC50 values of 2.58±0.52, 2.44±0.35, and 2.23±0.14 µM, respectively, than the positive control oleanolic acid (IC50=2.74±0.20 µM). On the basis of the data obtained, these bibenzyls with the longer C-2 prenyl groups may be considered as potential lead compounds for the development of new anti-obesity and anti-diabetic agents. Also, the PTP1B inhibitory effects for prenylated bibenzyls are being reported for the first time.

authors

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

doi

10.1248/cpb.c16-00868

subject

Has Abstract

pub_date

2017-01-01 00:00:00

pages

295-299

issue

3

eissn

0009-2363

issn

1347-5223

journal_volume

65

pub_type

杂志文章
  • Sesquiterpenoids from the formosan soft coral Sinularia leptoclados.

    abstract::Chemical investigation of the soft coral Sinularia leptoclados has afforded three new sesquiterpenoids, leptocladols A (1), B (2), and 1-epi-chabrolidione A (3). The relative structures of 1-3 were determined on the basis of extensive spectroscopic analysis. The relative configuration of 1 was further confirmed by a s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.250

    authors: Su JH,Chiang MY,Wen ZH,Dai CF,Hsu CH,Sheu JH

    更新日期:2010-02-01 00:00:00

  • Finding of primitive polyamine toxins in the venom of a joro spider, Nephila clavata.

    abstract::A series of joro spider toxins, novel polyamines sharing a common moiety of 2,4-dihydroxyphenylacetyl cadaverine, have been identified using various bioassays, such as inhibition of a glutamatergic transmission and insecticidal activity. In this paper, we tried to chemically find still unknown polyamine toxins in the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1864

    authors: Chiba T,Akizawa T,Matsukawa M,Pan-Hou H,Yoshioka M

    更新日期:1994-09-01 00:00:00

  • A new synthesis of indoloquinolizines by Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridines utilizing sec-nitrodienamine.

    abstract::The Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridine 5c derived from the cycloaddition of the sec-nitrodienamine 3c with acetaldehyde afforded the indoloquinolizine derivatives 6 and 7. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1898

    authors: Koike T,Shinohara Y,Tobinaga S,Takeuchi N

    更新日期:2000-12-01 00:00:00

  • Prediction of the stability of imipenem in intravenous mixtures.

    abstract::The purpose of this study was to predict the stability of imipenem in a mixed infusion. The hydrolysis of imipenem in aqueous solution was found to be accelerated by pH, and by increasing concentrations of sodium bisulfite (SBS) and L-cysteine. Equations were derived for the degradation rate constants (k(obs)) of pH, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00427

    authors: Yoshida M,Takasu Y,Shimizu K,Asahara K,Uchida T

    更新日期:2013-01-01 00:00:00

  • Four new neo-clerodane diterpenoid alkaloids from Scutellaria barbata with cytotoxic activities.

    abstract::Four new neo-clerodane diterpenoid alkaloids, named scutebarbatines C-F (1-4), were isolated from the whole plants of Scutellaria barbata D. DON. Their structures were elucidated by spectral analyses (UV, IR, FAB-MS, 1D-NMR and 2D-NMR). In vitro, compounds 1-4 showed significant cytotoxic activities against three huma...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.869

    authors: Dai SJ,Chen M,Liu K,Jiang YT,Shen L

    更新日期:2006-06-01 00:00:00

  • PEC films prepared from Chitosan-Alginate coacervates.

    abstract::Chitosan-alginate polyelectrolyte complex (PEC) have been prepared in situ in beads and microspheres. This study examines the preparation of suitable chitosan-alginate coacervates for casting into homogeneous PEC films for potential applications in packaging, controlled release systems and wound dressings. Coacervatio...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.941

    authors: Yan X,Khor E,Lim LY

    更新日期:2000-07-01 00:00:00

  • A stimulatory effect of Artemisia leaf extract on the proliferation of cultured endothelial cells.

    abstract::To investigate the effect of the hot water extract from Artemisia leaf (Artemisia princeps Panpanini) (AFE) on the proliferation of endothelial cells, the cells from bovine aorta were cultured for up to 96 h in the presence of 1, 5, 10 or 50 micrograms/ml AFE in RPMI1640 medium supplemented with 10% fetal bovine serum...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.538

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

    更新日期:1990-02-01 00:00:00

  • Chemical constituents of Tupistra chinensis rhizomes.

    abstract::A new pregnane glycoside, a dibenzylbutyrolactone lignan, 5-hydroxymatairesinol dimethyl ether, and three new flavonoids, including one 8-methylflavan-3-ol, and two 8-methylflavones, together with five known flavonoids and two known alkaloids were isolated from the rhizomes of Tupistra chinensis. The structures of all...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.954

    authors: Pan WB,Wei LM,Wei LL,Wu YC

    更新日期:2006-07-01 00:00:00

  • Three new cycloartane triterpene glycosides from Souliea vaginata.

    abstract::Three new cycloartane triterpene glycosides, soulieosides A (1), B (2), and C (3), were isolated from the rhizomes of Souliea vaginata, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Soulieosides A-C were assigned as 25-O-acetylcimigenol-3-O-beta-D-(2-acetyl)xylopy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.622

    authors: Zhou L,Yang J,Zou J,Tu G

    更新日期:2004-05-01 00:00:00

  • gamma-Pyrones from Gonystylus keithii, as new inhibitors of parathyroid hormone (PTH)-induced Ca release from neonatal mouse calvaria.

    abstract::New gamma-pyrones, 9'-oxopodopyrone (3) and 8-methyl-9'-oxopodopyrone (4) were isolated from the leaves of Gonystylus keithii, along with known gamma-pyrones, 10'-oxopodopyrone (1) and 8-methyl-10'-oxopodopyrone (2). These gamma-pyrones markedly inhibited the bovine parathyroid hormone (PTH)-induced Ca release from ne...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1046

    authors: Kanazawa T,Ohkawa Y,Kuda T,Minobe Y,Tani T,Nishizawa M

    更新日期:1997-06-01 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

  • 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

  • Synthesis of N-(trifluoromethyl-2-pyridinyl)arenesulfonamides as an inhibitor of secretory phospholipase A₂.

    abstract::A series of N-(trifluoromethyl-2-pyridinyl)alkane- and arenesulfonamides 2-5 have been synthesized by the substitution reaction of 2-chloro(trifluoromethyl)pyridines 6 with alkane- and arenesulfonamides 7. Their inhibitory activities against secretory phospholipase A₂ of porcine pancreas were examined and the analog N...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.783

    authors: Nakayama H,Morita Y,Kimura H,Ishihara K,Akiba S,Uenishi J

    更新日期:2011-01-01 00:00:00

  • Synthesis of peptides mimicking chemokine receptor CCR5 and their inhibitory effects against HIV-1 infection.

    abstract::Peptides mimicking chemokine receptor CCR5 were synthesized and their anti-HIV-1 activities evaluated. Prepared compounds, especially a sulfated derivatives, showed significant anti-HIV-1 activities. Furthermore, a hybrid molecule linked to an N-carbomethoxycarbonyl-prolyl-phenylalanine (CPF) moiety had a greater effe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.308

    authors: Konishi K,Ikeda K,Achiwa K,Hoshino H,Tanaka K

    更新日期:2000-02-01 00:00:00

  • Selected ion monitoring for the determination of bromovalerylurea in human plasma.

    abstract::A gas chromatography-selected ion monitoring procedure with chemical ionization is described for the determination of bromovalerylurea (BVU) in human plasma. BVU was extracted with ether after addition of 2-bromo-2-methylpropylurea as an internal standard. The lower limit of BVU quantification by this method was 2 ng/...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1517

    authors: Kokatsu J,Yomoda R,Suwa T

    更新日期:1992-06-01 00:00:00

  • Preparation of Amorphous Composite Particles of Drugs with Ursodeoxycholic Acid as Preclinical Formulations.

    abstract::We studied the possibility of using ursodeoxycholic acid (UDCA) as an excipient to create an amorphous composite that can be administered to animals in preclinical studies of experimental drugs. Three UDCA-based amorphous samples composed of nifedipine (NIF), indomethacin (IND), and naproxen (NAP) were found by screen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00644

    authors: Tanida S,Yoshimoto A,Yoshida M,Uchiyama H,Kadota K,Tozuka Y

    更新日期:2019-01-01 00:00:00

  • Biochemical and partial molecular characterization of bitter and sweet forms of Lupinus angustifolius, an experimental model for study of molecular regulation of quinolizidine alkaloid biosynthesis.

    abstract::The bitter and sweet forms of a plant species differing with alkaloid contents may provide a model system for investigation of alkaloid biosynthesis at a molecular level. The pattern and concentration of quinolizidine alkaloids were determined by capillary GC-MS in bitter and sweet plants of Lupinus angustifolius. Bit...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1458

    authors: Hirai MY,Suzuki H,Yamazaki M,Saito K

    更新日期:2000-10-01 00:00:00

  • Preparations of anthraquinone and naphthoquinone derivatives and their cytotoxic effects.

    abstract::Chrysophanol and 1,8-di-O-hexylchrysophanol derivatives having nucleic acid bases at position 5 were synthesized. Furthermore, derivatives of menadione substituted at position 11 (type A naphthoquinone derivatives) or methylmenadione substituted at position 7 (type B naphthoquinone derivatives) modified with nucleic a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.302

    authors: Cui XR,Saito R,Kubo T,Kon D,Hirano Y,Saito S

    更新日期:2011-01-01 00:00:00

  • Reactions of oxalyl chloride with 1,2-cycloalkanediols in the presence of triethylamine.

    abstract::The relationship between the product patterns and the configurations of 1,2-cycloheptane- and 1,2-cyclooctanediols 9 in the cyclocondensations with oxalyl chloride in the presence of triethylamine at 0 degrees C has been shown analogous to that obtained for 1,2-disubstituted acyclic ethylene glycols 1: cis-1,2-cyclooc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.83

    authors: Itaya T,Iida T,Natsutani I,Ohba M

    更新日期:2002-01-01 00:00:00

  • Efficient synthesis of trans- or cis-4(5)-(5-aminomethyltetrahydrofuran-2-yl)imidazoles via diazafulvene intermediates: synthetic approach toward human histamine H4)-ligands.

    abstract::(+)-4(5)-[(2R,5R)-5-aminomethyltetrahydrofuran-2-yl]imidazole [(+)-1, imifuramine] and its 2R,5S-stereoisomer (+)-2 were expected as base compounds to develop selective human histamine H4-receptor ligands. The improved synthesis of (+)-1 was done via cyclization of a diazafulvene intermediate generated by Bu3P/N,N,N',...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.832

    authors: Harusawa S,Araki L,Terashima H,Kawamura M,Takashima S,Sakamoto Y,Hashimoto T,Yamamoto Y,Yamatodani A,Kurihara T

    更新日期:2003-07-01 00:00:00

  • Possible involvement of a tumor necrosis factor (TNF)-like mediator as an endogenous pyrogen in fever induction by Nocardia rubra cell wall skeleton (N-CWS).

    abstract::Tumor necrosis factor (TNF), a cytokine produced in macrophages, also acts as an endogenous pyrogen (EP). To investigate whether TNF has a role in the fever induced by Nocardia rubra cell wall skeleton (N-CWS), the relationship between fever and TNF production was studied in guinea pigs. N-CWS injected i.v. to guinea ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2795

    authors: Ohara K,Hirano Y,Ishida H,Mori J,Tensho A

    更新日期:1989-10-01 00:00:00

  • A novel method for estimation of transition temperature for polymorphic pairs in pharmaceuticals using heat of solution and solubility data.

    abstract::A novel method for thermodynamic stability studies of polymorphic drug substances has been developed. In order to estimate the transition temperature for an enantiotropic polymorphic pair, a formula for calculating the temperature at which the solubilities of each polymorph become equal has been derived with heat of s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.263

    authors: Urakami K,Shono Y,Higashi A,Umemoto K,Godo M

    更新日期:2002-02-01 00:00:00

  • Saponins esculeosides B-1 and B-2 in Italian canned tomatoes.

    abstract::Italian canned tomatoes contain the tomato glycosides esculeosides B-1 (1, 0.0052%) and B-2 (2, 0.0068%) without esculeoside A. Herein, the structure of esculeoside B-1 (1) is characterized to be 3-O-β-lycotetraosyl (5S,22R,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane 27-O-β-D-glucopyranoside. We ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00202

    authors: Manabe H,Fujiwara Y,Ikeda T,Ono M,Murakami K,Zhou JR,Yokomizo K,Nohara T

    更新日期:2013-01-01 00:00:00

  • Studies on responsiveness of hepatoma cells to catecholamines. V. Loss of adrenergic response of glycogen phosphorylase in rat ascites hepatoma AH130 cells.

    abstract::The beta-adrenoceptor-cyclic adenosine monophosphate (AMP) dependent glycogenolytic cascade was examined in normal rat hepatocytes and rat ascites hepatoma AH130 cells. The cyclic AMP content in AH130 cells was half of that in normal hepatocytes, and the cyclic AMP levels in both kinds of cells were clearly increased ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.470

    authors: Miyamoto K,Wakusawa S,Izumiya S,Koshiura R,Sakai R

    更新日期:1990-02-01 00:00:00

  • New lignans from the heartwood of Chamaecyparis obtusa var. formosana.

    abstract::Four new lignans, 3',4'-O,O-demethylenehinokinin (1), chamalignolide (2), 8'beta-hydroxyhinokinin (3) and 7beta,8beta-epoxyzuonin A (4), as well as (-)-hinokinin (5), and (-)-zuonin A (6), were isolated from the heartwood of Chamaecyparis obtusa var. formosana. The structures of these lignans were unambiguously determ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.978

    authors: Kuo YH,Chen CH,Lin YL

    更新日期:2002-07-01 00:00:00

  • Characterization of secondary structure of neocarzinostatin apoprotein.

    abstract::Characteristics of the secondary structure of neocarzinostatin apoprotein (apo-NCS) were examined by various means. Gaussian analysis of the Fourier-transform infrared (FT-IR) curve and curve-fitting of the circular dichroism (CD) spectrum for apo-NCS revealed that this peptide was abundant in beta-structures. In the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3078

    authors: Saito K,Sato Y,Edo K,Akiyama-Murai Y,Koide Y,Ishida N,Mizugaki M

    更新日期:1989-11-01 00:00:00

  • N-Methylniphatyne A, a New 3-Alkylpyridine Alkaloid as an Inhibitor of the Cancer Cells Adapted to Nutrient Starvation, from an Indonesian Marine Sponge of Xestospongia sp.

    abstract::In the course of searching for selective growth inhibitors of the cancer cells adapted to nutrient starvation, a new 3-alkylpyridine alkaloid named N-methylniphatyne A (1) was isolated from an Indonesian marine sponge of Xestospongia sp. The chemical structure of 1 was determined on the basis of the spectroscopic anal...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00118

    authors: Arai M,Kamiya K,Shin D,Matsumoto H,Hisa T,Setiawan A,Kotoku N,Kobayashi M

    更新日期:2016-01-01 00:00:00

  • Gelation Factors of Pectin for Development of a Powder Form of Gel, Dry Jelly, as a Novel Dosage Form.

    abstract::Jellies for oral administration are dosage forms that contain water, as stipulated in the Japanese Pharmacopeia, and heat is generally applied to the jellies during the manufacturing process. Therefore, it is difficult to formulate drugs that may be affected adversely by water and/or heat. To solve this problem, we tr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00447

    authors: Kakino Y,Hishikawa Y,Onodera R,Tahara K,Takeuchi H

    更新日期:2017-01-01 00:00:00

  • Control of Drug Diffusion Behavior of Xanthan and Locust Bean Gum Gel by Agar Gel.

    abstract::Oral gel formulations are known as easy to administer drug products for patients who have problems taking drugs including those with conditions such as dysphagia. In addition, there are numerous commercially available oral gel products, most of which are immediate-release formulation that release their pharmaceutical ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00135

    authors: Hishikawa Y,Kakino Y,Tsukamoto H,Tahara K,Onodera R,Takeuchi H

    更新日期:2016-01-01 00:00:00

  • Biologically active glycosides from Asteroidea, 41. Isolation and structure determination of glucocerebrosides from the starfish Linckia laevigata.

    abstract::A new glucocerebroside, linckiacerebroside A (1) and a known glucocerebroside S-2a-3 (2), have been isolated from the cerebroside molecular species obtained from the less polar fraction of the CHCl3/MeOH extract of the starfish Linckia laevigata, together with three pseudo homogeneous glucocerebroside, 3, 4, and 5. Th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1255

    authors: Maruta T,Saito T,Inagaki M,Shibata O,Higuchi R

    更新日期:2005-10-01 00:00:00