Chemical and Pharmaceutical Bulletin
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Volume 51, Issue 7
Displaying 1-33 of 33 articles from this issue
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Regular Articles
  • Development of a Novel Compression Tester and Rheo-Mechanical Properties of Wet-Mass Powder. I
    —Effect of Kneading Time on the Rheo-Mechanical Properties—
    Satoru Watano, Tomoko Yoshikawa, Yoshifumi Osako, Masamitsu Tsuhari
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 747-750
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.747
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    In our previous paper [Watano S., et al., Chem. Phram. Bull., 49(1), 64—68, (2001)], a compaction tester was developed to quantitatively evaluate the water dispersion condition of wet kneaded masses prepared by a paddle type kneader. It was also demonstrated that the physical properties of pellets prepared by extrusion granulation after the kneading could be well predicted by the vertical pressure transmission obtained through the compaction tester. However, in this compression tester, the vertical pressure transmission was just obtained and rheological and mechanical properties (so called rheo-mechanical properties) of wet mass-powder that should be the most important to determine the deformation process were not well studied. In this study, a novel compression tester, which can measure both vertical and radial pressure transmissions, has been developed. Based on the compression test, mechanical property (Young's modulus) and rheological property (effective internal friction) of wet mass powder prepared by different kneading times were quantitatively investigated. Granules (pellets) were then obtained through the extrusion granulation and fluidized bed drying, and the physical properties (strength and disintegration time) of the obtained pellet were evaluated. The relationship between the granule (pellet) physical properties and the mechanical and rheological (rheo-mechanical) properties was analyzed.
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  • Development of a Novel Compression Tester and Rheo-Mechanical Properties of Wet-Mass Powder. II
    —Effect of Moisture Content on the Rheo-Mechanical Properties—
    Satoru Watano, Tomoko Yoshikawa, Yoshifumi Osako, Masamitsu Tsuhari
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 751-753
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.751
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    In our previous paper [Watano S., et al., Chem. Pharm. Bull., 51(7), 747—750 (2003)], a novel compression tester, which enables the vertical and radial pressure transmission measurement, has been developed and quantitative analysis of rheo-mechanical properties of wet-mass powder prepared by different kneading times was conducted. In this study, the compression test was conducted by using the kneaded wet-mass powders prepared by different moisture contents. Pressure transmission characteristics and rheo-mechanical properties have been investigated to characterize the wet-mass powders. The relationship between these parameters and granule physical properties was also investigated.
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  • Dynamic Character of Human Growth Hormone and Its Receptor: Normal Mode Analysis
    Youji Kurihara, Tomoko Watanabe, Hiroyuki Nojima, Mayuko Takeda-Shitak ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 754-758
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.754
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    Human growth hormone (hGH) induces dimerization of its binding protein (hGHbp). hGH binds to the first hGHbp (bp1) on site 1, and then the hGH–bp1 heterodimer complex binds to the second hGHbp (bp2) on site 2. Although the interactions of hGH and hGHbps have been studied from different viewpoints, few studies from a dynamic viewpoint have been reported. Especially, since in the SCOP domain database hGHbp is classified as two clear immunoglobulin-like domains, it is of interest to understand how hGH interacts with the hGHbp domains. Therefore, we carried out normal mode analysis (NMA) of free hGH, free bp1, free bp2, and the hGH–bp1 heterodimer complex, as well as the hGH–bp1–bp2 ternary complex to investigate how the dynamics of the proteins change before and after forming the complexes. NMA showed that the domain motion between the N-terminal and the C-terminal domains of free bp1 markedly decreased after binding to hGH, and that the domain motion of bp2 decreased similarly after binding to the hGH–bp1 heterodimer complex. The present study demonstrates that hGH regulates the inter-domain motions of both hGHbps.
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  • Synthesis and Antinociceptive Activity of Orally Active Opioid Peptides: Improvement of Oral Bioavailability by Esterification
    Tadashi Ogawa, Mamoru Araki, Tetsuhisa Miyamae, Toru Okayama, Masaki H ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 759-771
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.759
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    To improve the oral bioavailability of a dermorphin tetrapeptide analog, Nα-1-iminoethyl-Tyr-D-MetO-Phe-MeβAla-OH (III),1) which has a potent analgesic activity after oral administration, various derivatives were synthesized to increase lipophilicity by esterification of the C-terminal carboxyl group and/or acylation of the phenolic hydroxyl group on Tyr1. Antinociceptive activity was evaluated after subcutaneous or oral administration using the mouse tail pressure test. As a result, increased antinociceptive activity after oral administration as well as an improved ED50(p.o.)/ED50(s.c.) ratio, which is an indicator of oral bioavailability, were found for some compounds. With regard to the improvement of bioavailability, derivatives with acylation of the phenolic hydroxyl group on Tyr1 showed better results than derivatives with esterification of the C-terminal carboxyl group. In particular, an ED50(p.o.)/ED50(s.c.) ratio equivalent to that of morphine was found for an acetylated derivative, Nα-1-iminoethyl-Tyr(COMe)-D-MetO-Phe-MeβAla-OH (7a), as well as for a methoxycarbonylated derivative, Nα-1-iminoethyl-Tyr(CO2Me)-D-MetO-Phe-MeβAla-OH (7l).
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  • Preparation and Evaluation of Combination Tablet Containing Incompatible Active Ingredients
    Xiaoyan Wang, Fude Cui, Yorinobu Yonezawa, Hisakazu Sunada
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 772-778
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.772
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    Combination preparation plays an important role in clinical treatment because of its better and wider curative synergism and weaker side effects. However, the existence of incompatibility between active ingredients or between active ingredients and excipients presents a serious obstacle in the preparation of such combination solid dosage forms. In this study, aspirin and ranitidine hydrochloride, between which there existed a chemical interaction, were selected as model drugs. Aspirin powders without any additives were granulated with hydroxypropyl methyl cellulose (HPMC) water solution as a binder using a Wurster coating apparatus and the operation conditions were optimized by Artificial Neural Network (ANN) analysis. Under these conditions, the aspirin granules prepared showed good flowability and compressibility. On the other hand, ranitidine hydrochloride was coated with Aquacoat (ethyl cellulose aqueous dispersion) after preliminary granulation with the Wurster coating apparatus. The aspirin granules and coated ranitidine hydrochloride particles were compressed into tablets with suitable excipients. The combination tablets showed good dissolution, content uniformity and improved stability of active ingredients.
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  • Nonnucleoside HIV-1 Reverse Transcriptase Inhibitors: Part I.
    Synthesis and Structure–Activity Relationship of 1-Alkoxymethyl-5-alkyl-6-naphthylmethyl Uracils as HEPT Analogues
    Ge Meng, Fen-Er Chen, Erik De Clercq, Jan Balzarini, Christophe Pannec ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 779-789
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.779
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    1-Alkoxymethyl-5-alkyl-6-naphthylmethyl uracils, which are novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) analogues, were synthesized for evaluation as selective and potent nonnucleoside human immunodeficiency virus (HIV)-1 reverse transcriptase inhibitors. The anti-HIV-1 activity of these compounds was assayed in vitro using HIV-1 infected MT-4 and CEM bioassays. The EC50, CC50 and SI were recorded and calculated. The appropriate position, especially in the 1-position of the naphthyl ring, led to dramatic increases in potency, in both MT-4 and CEM cellular assays. The most important compounds in this series, 1-ethoxymethyl-5-isopropyl-6-(1-naphthylmethyl)thymine 8l (IC50=17 nM, CC50=38332 nM, SI=2229) and 1-benzyloxymethyl-5-ethyl-6-(1-naphthylmethyl)thymine 8n (IC50=17 nM, CC50=32560 nM, SI=1889) were significantly more potent than HEPT (EC50=7.0 μM, CD50=740 μM) in the anti-HIV-1 in vitro cellular assay.
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  • Ent-kaurane Diterpenoids from Isodon rubescens var. lushanensis
    Quan-Bin Han, Ma-Lin Li, Sheng-Hong Li, Yi-Kun Mou, Zhong-Wen Lin, Han ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 790-793
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.790
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    Four new ent-kaurane diterpenoids lushanrubescensins F—I (1—4), together with 11 known ones, lasiodonin (5), oridonin (6), ponicidin (7), isodonoiol (8), isodonal (9), rabdosin B (10), rabdoternins A and B (11 and 12), enmenol (13), epinodosin (14), and inflexusin (15), were isolated from Isodon rubescens var. lushanensis, and the structures were elucidated by spectroscopic analysis. The inhibitory effect against the K562, Bcap37, BGC823, BIU87, CA, CNE, and Hela cell lines of compounds 3 and 5—10 were evaluated.
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  • Phenyl Ethers from Cultured Lichen Mycobionts of Graphis scripta var. serpentina and G. rikuzensis
    Yukiko Takenaka, Takao Tanahashi, Naotaka Nagakura, Nobuo Hamada
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 794-797
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.794
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    Spore-derived mycobionts of the lichen Graphis scripta var. serpentina and G. rikuzensis were cultivated on a malt-yeast extract medium supplemented with 10% sucrose and their metabolites were investigated. 3,3′-Dihydroxy-5,5′-dimethyldiphenyl ether was isolated from the cultures of the mycobionts of G. scripta var. serpentina, while a new phenyl ether, rikuzenol, along with two known diphenyl ethers, violaceol-I and violaceol-II, were isolated from those of G. rikuzensis. The structure of the new compound was determined by spectroscopic methods. Violaceol-I was chemically synthesized and interconversion between violaceol-I and violaceol-II was proven.
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  • Syntheses of Arbutin-α-glycosides and a Comparison of Their Inhibitory Effects with Those of α-Arbutin and Arbutin on Human Tyrosinase
    Kazuhisa Sugimoto, Takahisa Nishimura, Koji Nomura, Kenji Sugimoto, Ta ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 798-801
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.798
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    The effects of 4-hydroxyphenyl α-glucopyranoside (α-arbutin) and 4-hydroxyphenyl β-glucopyranoside (arbutin) on the activity of tyrosinase from human malignant melanoma cells were examined. The inhibitory effect of α-arbutin on human tyrosinase was stronger than that of arbutin. The Ki value for α-arbutin was calculated to be 1/20 that for arbutin. We then synthesized arbutin-α-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase using arbutin and starch, respectively, as acceptor and donor molecules. The structural analyses using 13C- and 1H-NMR proved that the transglycosylated products were 4-hydroxyphenyl β-maltoside (β-Ab-α-G1) and 4-hydroxyphenyl β-maltotrioside (β-Ab-α-G2). These arbutin-α-glycosides exhibited competitive type inhibition on human tyrosinase, and their Ki values were calculated to be 0.7 mM and 0.9 mM, respectively. These arbutin-α-glycosides posessed stronger inhibitory activity than arbutin, but less activity than α-arbutin. These results suggested that the α-glucosidic linkage of hydroquinone-glycosides plays an important role in the inhibitory effect on human tyrosinase.
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  • Inocalophyllins A, B and Their Methyl Esters from the Seeds of Calophyllum inophyllum
    Ya-Ching Shen, Meng-Chieh Hung, Li-Tang Wang, Ching-Yu Chen
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 802-806
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.802
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    Fractionation of the ethanolic extract of the seeds of Calophyllum inophyllum L. has resulted in the isolation of four novel pyranocoumarin derivatives, designated as inocalophyllins A (1), B (2) and their methyl esters (3, 4) in addition to the known calophyllolide. The structures of these compounds have been determined on the basis of spectroscopic analysis including MS, heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and two dimensional incredible natural abundance double quantum transfer experiment (2D-INADEQUATE). Two new methylated products, 5 and 6 were also prepared by methylation of compounds 1 and 2, respectively.
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  • Physicochemical and Crystal Structure Analyses of the Antidiabetic Agent Troglitazone
    Katsuhiro Kobayashi, Hiroshi Fukuhara, Tadashi Hata, Akiko Sekine, Hid ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 807-814
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.807
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    The antidiabetic agent troglitazone has two asymmetric carbons located at the chroman ring and the thiazolidine ring and is produced as a mixture of equal amounts of four optical isomers, 2R-5S, 2S-5R, 2R-5R, and 2S-5S. The crystalline powdered drug substance consists of two diastereomer pairs, 2R-5R/2S-5S and 2R-5S/2S-5R. There are many types of crystals obtained from various crystallization conditions. The X-ray structure analysis and the physicochemical analyses of troglitazone were performed. The solvated crystals of the 2R-5R/2S-5S pair were crystallized from several solutions: methanol, ethanol, acetonitrile, and dichloromethane. The ratio of solvent and troglitazone was 1 : 2 (L1/2-form). The monohydrate crystals were obtained from aqueous acetone solution (L1-form). On the other hand, only an anhydrate crystal of the 2R-5S/2S-5R pair was crystallized from various solutions (H0-form). The dihydrous mixed crystal (MA2-form) was obtained from a mixture of the two diastereomer pairs of 2R-5R/2S-5S and 2R-5S/2S-5R in equal amounts by the slow evaporation of aqueous acetone solution. The crystal structure of the MA2-form is similar to the H0-form. When the MA2 crystal was kept under low humidity, it was converted into the dehydrated form (MA0-form) with retention of the single crystal form. The structure of the MA0-form is isomorphous to the H0-form. The MA2-form was converted into the MA0-form and vice versa with retention of the single crystal under low and high humidity, respectively. The crystallization and storage conditions of the drug substances were successfully analyzed.
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  • Effects of Poly(ethylene glycol) (PEG) Chain Length of PEG-Lipid on the Permeability of Liposomal Bilayer Membranes
    Kaname Hashizaki, Hiroyuki Taguchi, Chika Itoh, Hideki Sakai, Masahiko ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 815-820
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.815
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    The effects of poly(ethylene glycol) (PEG) chain length of PEG-lipid on the membrane characteristics of liposomes were investigated by differential scanning calorimetry (DSC), freeze-fracture electron microscopy (FFEM), fluorescence polarization measurement and permeability measurement using carboxyfluorescein (CF). PEG-liposomes were prepared from mixtures of dipalmitoyl phosphatidylcholine (DPPC) and distearoyl phosphatidylethanolamines with covalently attached PEG molecular weights of 1000, 2000, 3000 and 5000 (DSPE-PEG). DSC and FFEM results showed that the addition of DSPE-PEG to DPPC in the preparation of liposomes caused the lateral phase separation both in the gel and liquid-crystalline states. The fluidity in the hydrocarbon region of liposomal bilayer membranes was not significantly changed by the addition of DSPE-PEG, while that in the interfacial region was markedly increased. From these results, it was anticipated that the CF leakage from PEG-liposomes is accelerated compared with DPPC liposomes. However, CF leakage from liposomes containing DSPE-PEG with a 0.060 mol fraction was depressed compared with regular liposomes, and the leakage decreased with increasing PEG chain length. Furthermore, the CF leakage from liposomes containing DSPE-PEG with a 0.145 mol fraction was slightly increased compared with that of liposomes containing DSPE-PEG with a 0.060 mol fraction. It is suggested that the solute permeability from the PEG-liposomes was affected by not only properties of the liposomal bilayer membranes such as phase transition temperature, phase separation and membrane fluidity, but also the PEG chain of the liposomal surface.
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  • Synthetic Approaches toward Ecteinascidins. Part 2.
    Preparation of the ABCDE Ring System of Ecteinascidins Having Characteristic Substituents in Both Benzene Rings
    Naoki Saito, Ryu-ichi Seki, Noriko Kameyama, Rie Sugimoto, Akinori Kub ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 821-831
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.821
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    A synthesis of an advanced ABCDE ring system (24c) having characteristic substituents in both benzene rings of ecteinascidin marine natural products is described based on our model studies.
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  • Efficient Synthesis of trans- or cis-4(5)-(5-Aminomethyltetrahydrofuran-2-yl)imidazoles via Diazafulvene Intermediates: Synthetic Approach toward Human Histamine H4-Ligands
    Shinya Harusawa, Lisa Araki, Hirotaka Terashima, Makoto Kawamura, Seii ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 832-837
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.832
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    (+)-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′,N′-tetramethylazodicarboxamide (TMAD) treatment of a diol 17ab bearing an unsubstituted imidazole moiety in good yields. This methodology also afforded an alternative synthetic route to trans- and cis-ethyl 4(5)-(5-hydroxymethyltetrahydrofuran-2-yl)imidazole carboxylates (5 and 6), reported previously. Also, 4(5)-[(2R,5S)-5-aminomethyltetrahydrofuran-2-yl]imidazole (+)-2 was synthesized from ethyl 4(5)-(2-deoxy-β-D-ribofuranosyl)imidazole-1-carboxylate (35) via the four steps involving deoxygenation.
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  • Synthesis of Novel 1,3,4-Trisubstituted Pyrazole Derivatives and Their Evaluation as Antitumor and Antiangiogenic Agents
    Ashraf Hassan Abadi, Amal Abdel Haleem Eissa, Ghaneya Sayed Hassan
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 838-844
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.838
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    Several 1,3,4-trisubstituted pyrazole derivatives were synthesized and screened for their cytotoxic effect in a primary 3 tumor cell line test at 10−4 M drug concentration. Compounds 19 and 20 reduced the growth of one or more of these cell lines to less than 32% and escalated up to evaluation in the full panel of 60 human tumor cell lines at a minimum of 5 concentrations at 10 fold dilutions. Compound N′-(1-{1-[4-nitrophenyl]-3-phenyl-1H-pyrazol-4-yl}methylene)-2-chlorobenzohydrazide 19 proved to be the most active of these derivatives with full panel median growth inhibition (GI50), total growth concentration (TGI) and median lethal concentration (LC50) mean graph mid-point (MG-MID) of 3.79, 12.5 and 51.5 μM, respectively. In addition, compounds 19, 39, 40, 41, 43, 45, 47 were tested for their antiangiogenic properties by testing their ability to inhibit human umbilical vein endothelial cells (HUVECs) proliferation, cord formation and migration in response to chemoattractant. 3-Acetyl-2-(1-(4-nitrophenyl)-3-phenylpyrazol-4-yl)-5-(4-pyridyl)-1,3,4-oxadiazoline 39 showed significant antiangiogenic profile at non-cytotoxic doses, with HUVEC proliferation inhibition IC50 of 7.60 μM, chemotaxis IC50 of 0.86 μM and was superior to the reference celecoxib 2 in both tests. Furthermore, in contrary to the references TNP-470 and celecoxib, all the tested compounds interfered with the migratory function of HUVECs in response to vascular endothelium growth factor (VEGF) rather than the endothelial cells proliferation.
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  • Four New Diterpenoids from Isodon melissoides
    Ai-Hua Zhao, Quan-Bin Han, Sheng-Hong Li, Fu-Sheng Wang, Qin-Shi Zhao, ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 7 Pages 845-847
    Published: 2003
    Released on J-STAGE: July 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.845
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    Three new 11β,16β-epoxy-ent-kauranoids melissoidesins I—K (1—3) and one new ent-abietanoid melissoidesin L (4) were obtained from the aerial parts of Isodon melissoides (BENTHAM) H. HARA, their structures were established on the basis of the spectral methods, especially two dimensional (2D) NMR spectroscopy.
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