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Volume 52, Issue 7
Displaying 1-22 of 22 articles from this issue
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Kiran Iqbal, Abdul Malik, Naveen Mukhtar, Itrat Anis, Shamsun Nahar Kh ...2004 Volume 52 Issue 7 Pages 785-789
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSThree C-alkylated flavonoids 7-O-α-D-glucopyranosyl-3,5-dihydroxy-3′-(4″-acetoxyl-3″-methylbutyl)-6,4′-dimethoxyflavone (1), 7-O-α-D-glucopyranosyl-3,4′-dihydroxy-3′-(4″-acetoxyl-3″-methylbutyl)-5,6-dimethoxyflavone (2), 3,7,4′-trihydroxy-3′-(8″-acetoxy-7″-methyloctyl)-5,6-dimethoxyflavone (3) and a trans-clerodane type diterpenoid (−)-6β-hydroxy-5β,8β,9β,10α-cleroda-3,13-dien-16,15-olid-18-oic acid (4) are reported from Duranta repens along with (+)-hardwickiic acid (5) and (+)-3,13-clerodadien-16,15-olid-18-oic acid (6), isolated for the first time from this species. Their structures were established on the basis of the spectral methods, especially two dimensional (2D) NMR spectroscopy.View full abstractDownload PDF (127K) -
Teresa Swee Har Kwok, Bruce Vivian Sunderland, Paul Wan Sia Heng2004 Volume 52 Issue 7 Pages 790-796
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSPolymers for aqueous film coating, such as hydroxypropyl methylcellulose (HPMC), often require the inclusion of a plasticizer to reduce brittleness and increase flexibility and ductility. A vinyl pyrrolidone/vinyl acetate copolymer (S630) was investigated for its influence on HPMC film coating parameters, comparing the results with a commonly used plasticizer, polyethylene glycol and another copolymer, polyvinyl alcohol. The viscous properties of the solutions and the glass transition temperatures of the equivalent polymer films were evaluated. Its effect on the film properties, such as appearance, surface roughness, moisture permeation and mechanical properties, as well as its ability to promote better adhesion of the film coat to the core surface, was compared. S630 was able to reduce the viscosity of the polymer solution and glass transition temperature of HPMC, as well as, enhance the mechanical properties of the cast film. The moisture permeation was slightly reduced but not to the same extent as polyethylene glycol. A 10% concentration of S630 increased the adhesive strength and toughness of the HPMC film coat. In conclusion, S630 was effective as a film-former, substrate adhesive and plasticizer. It has the potential to be used to replace the more volatile plasticizers which have problems of loss or migration.View full abstractDownload PDF (191K) -
Anailien Boza, Rafael Blanquero, Monica Millan, Isidoro Caraballo2004 Volume 52 Issue 7 Pages 797-801
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSOne of the practical handicaps for the application of the percolation theory to estimate the percolation threshold of drugs in controlled release systems is the fact that the dissolution studies must be carried out so that only one surface of the tablet is exposed to the dissolution medium. The aim of this work is to estimate the percolation threshold of the antiarthritic drug lobenzarit dissodium (LBD) in inert matrices prepared with the excipients Ethocel® 100 and Eudragit® RS-PO (10—75% w/w). Release assays were performed using the paddle method. The whole surface of the tablets was exposed to the dissolution medium. For the first time, a new mathematical method is developed to transform the amount of drug released in amount released per surface area in order to calculate the percolation thershold of LBD. The mathematical method proposed allows to calculate, using a new equation, the evolution of the mean surface area (O(t)). The new method was validated and three novel results were achieved: A constant value of (O(t)) at critical time (θ) in the matrices (O(θ)=1.272 cm2); a linear relationship between initial surface area (O(0)) and critical time; and a linear relationship between O(t) and time. Employing the values of O(t), it was possible to calculate for the first time, the percolation threshold (pc1) for LBD in Ethocel® 100 (pc1=0.280±0.102) and Eudragit® RS-PO (pc1=0.344±0.07) matrices.View full abstractDownload PDF (315K) -
Atta-Ur-Rahman, Atia-Tul-Wahab, Sarfraz Ahmad Nawaz, M. Iqbal Choudh ...2004 Volume 52 Issue 7 Pages 802-806
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSPhytochemical investigation on Cocculus pendulus (J. R. & G. FORST.) resulted in the isolation of two new and three known bisbenzylisoquinoline alkaloids. The structures of the new alkaloids, kurramine-2′-β-N-oxide (1) and kurramine-2′-α-N-oxide (2), were elucidated with the help of spectroscopic techniques. The cholinesterase inhibitory activities of these bisbenzylisoquinoline alkaloids are reported here for the first time.View full abstractDownload PDF (110K) -
Takafumi Nakatani, Tomoyuki Konishi, Kazumoto Miyahara, Naoki Noda2004 Volume 52 Issue 7 Pages 807-809
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSThree novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect spectroscopy experiments, and chemical data confirmed them to be so-called cantharimides, in which the anhydride oxygen atoms are replaced by the basic amino acid L-lysine, L-ornithine, and L-arginine moieties.View full abstractDownload PDF (80K) -
Durmus Özdemir, Erdal Dinc2004 Volume 52 Issue 7 Pages 810-817
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSSimultaneous determination of binary mixtures pyridoxine hydrochloride and thiamine hydrochloride in a vitamin combination using UV–visible spectrophotometry and classical least squares (CLS) and three newly developed genetic algorithm (GA) based multivariate calibration methods was demonstrated. The three genetic multivariate calibration methods are Genetic Classical Least Squares (GCLS), Genetic Inverse Least Squares (GILS) and Genetic Regression (GR). The sample data set contains the UV–visible spectra of 30 synthetic mixtures (8 to 40 μg/ml) of these vitamins and 10 tablets containing 250 mg from each vitamin. The spectra cover the range from 200 to 330 nm in 0.1 nm intervals. Several calibration models were built with the four methods for the two components. Overall, the standard error of calibration (SEC) and the standard error of prediction (SEP) for the synthetic data were in the range of <0.01 and 0.43 μg/ml for all the four methods. The SEP values for the tablets were in the range of 2.91 and 11.51 mg/tablets. A comparison of genetic algorithm selected wavelengths for each component using GR method was also included.View full abstractDownload PDF (124K) -
Masaki Seto, Yoshio Aramaki, Hiroshi Imoto, Katsuji Aikawa, Tsuneo Oda ...2004 Volume 52 Issue 7 Pages 818-829
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSIn order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.View full abstractDownload PDF (248K) -
Toshimasa Tanaka, Teruaki Okuda, Yoshio Yamamoto2004 Volume 52 Issue 7 Pages 830-835
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSHuman microsomal cytochrome P450s participate in drug metabolism and detoxification. Among them, CYP3A4 is the most important isoform for drug–drug interactions. To gain a better understanding of the active site, a homology model of CYP3A4 was constructed based on the crystallographic coordinates of mammalian CYP2C5. The putative active site is much larger than that of CYP2C5 and is divided into three parts (i.e. a proximal and two distal sites from the heme). Most residues reported to be important for ligand-binding are located in the active site of the model. Moreover, some inhibitors (paclitaxel etc.) docked into the model have complementary shapes to the pocket. Pharmacophore docking of 14 substrates was also performed using Ph4Dock of MOE. Calculated interaction energies showed a moderate correlation with the logarithm of apparent Km values. These results suggest that this model is reliable enough to be used in the design of compounds for removing undesirable CYP3A4 inhibition.View full abstractDownload PDF (4559K) -
Toshimasa Tanaka, Naomi Kamiguchi, Teruaki Okuda, Yoshio Yamamoto2004 Volume 52 Issue 7 Pages 836-841
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSTo compare the features of the active sites of CYP2C8, CYP2C9, and CYP2C19, homology modeling was performed based on the crystallographic coordinates of mammalian CYP2C5. It was found that CYP2C8 has a much larger pocket than the other forms due to the existence of an additional pocket. The approach to the additional pocket is comprised of Ile102, Ser114, Leu208, Val366, and Ile476, and the side chains of Ser114, Val366, and Ile476, which are smaller than the corresponding residues in the other CYPs, enable access to the pocket. The general features of the active site in the CYP2C8 model are similar to those of the previously constructed CYP3A4 model, which may account for the 2 CYPs sharing some of their substrates. The CYP2C8 model was validated by examining the bound orientation of paclitaxel and showing that it is consistent with the formation of the 6-beta hydroxylated derivative during metabolism. Docked paclitaxel was found to form a hydrogen bond with the side chain of Asn 99, which is a characteristic residue of CYP2C8 and is located in the additional pocket. Descriptors for CYP2C8 and CYP2C9 substrates were also examined with the molecular operating environment (MOE). The descriptor by which CYP2C8 and CYP2C9 substrates were classified most distinctly was found to be molar refractivity, which might be related to the longer shape and more polar nature of the active site of CYP2C8 in the CYP2C subfamily.View full abstractDownload PDF (6657K) -
Hideto Miyabe, Hirotaka Tanaka, Takeaki Naito2004 Volume 52 Issue 7 Pages 842-847
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSTandem radical addition-cyclization of oxime ethers anchored to polymer support was studied. The reaction of oxime ethers with stannyl radical proceeded effectively by the use of triethylborane as a radical initiator. The alkyl radical addition-cyclization reactions of oxime ether connected with α,β-unsaturated carbonyl group proceeded under iodine atom-transfer reaction conditions to give the functionalized azacycles via two carbon–carbon bonds-forming process.View full abstractDownload PDF (131K) -
Hideki Arasaki, Masashi Iwata, Miyuki Makida, Yukio Masaki2004 Volume 52 Issue 7 Pages 848-852
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSStereospecific α C–H insertion reaction of protected chiral 1,2-glycols, (S)-1,2-isopropylidenedioxytridecane (3) and ethyl (S)-4,5-isopropylidenedioxy-pentanoate (4), prepared from (R)-glyceraldehyde acetonide (2), with dichlorocarbene generated from CHCl3/50% NaOH/cetyltrimethylammonium chloride (as ptc.) took place with complete retention of configuration to provide (S)-4-dichloromethyl-2,2-dimethyl-4-undecyl-1,3-dioxolane (5) and ethyl (S)-3-(4-dichloromethyl-2,2-dimethyl-1,3-dioxolan-4-yl)-propanoate (8), respectively. The ester (8) was transformed to 5 by elongation of the side chain. The glycol derivative (5) was converted into O-TBDPS-protected (S)-2-hydroxymethyl-2-undecyloxirane (16). Reaction of 16 with a cuprate reagent containing homoallylic carbon chain followed by oxidative manipulation of the terminal olefin afforded (R)-(+)-tanikolide (1).View full abstractDownload PDF (135K)
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Dejan D. Đoković, Vanja M. Bulatović, Biljana Đ ...2004 Volume 52 Issue 7 Pages 853-854
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESS3,5-Nonadiyne, in vitro, selectively inhibits endogenous nitric oxide release (IC50=6.7±0.8 μM) by rat peritoneal macrophages at doses that do not inhibit T cell proliferation. 3,5-Nonadiyne was isolated from root essential oil of Cachrys ferulacea (L.) CALESTANI, synonym Prangos ferulacea (L.) LINDLEY, obtained by hydrodistillation and spectrometricaly identified unambiguously.View full abstractDownload PDF (63K) -
Lun-Huei Lin, Hsu-Shan Huang, Chiung-Chang Lin, Lin-Wen Lee, Pen-Yuan ...2004 Volume 52 Issue 7 Pages 855-857
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSModification of the cantharidinimide structure led to the discovery of a novel class of antitumor compounds. These cantharidinimide derivatives containing aliphartic, aryl, and pyridyl groups showed some effect in vitro against HepG2 and HL-60 cells.View full abstractDownload PDF (81K) -
Yann-Lii Leu, Shih-Ming Kuo, Tsong-Long Hwang, Shau-Ting Chiu2004 Volume 52 Issue 7 Pages 858-860
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSTwo new flavanones, (2S)-pinocembrin 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and (2S)-pinocembrin 7-O-[cinnamoyl(1→5)-β-D-apiosyl(1→2)]-β-D-glucoside (2) together with eighteen known compounds, which include five known flavanones, nine benzenoids, one inositol and three triterpenoids, were isolated and characterized from fresh Viscum articulactum. Structures of new compounds were determined by spectral analysis. Among them, oleanolic acid (18) showed a significant inhibition effect on superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP).View full abstractDownload PDF (64K) -
Yueh-Hsiung Kuo, Ming-Hsi Yeh, Hsiu-Chuan Lin2004 Volume 52 Issue 7 Pages 861-863
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSNew abietane-type diterpenes, 15-acetoxy-7-oxodehydroabietic acid (1), picealactones A (2), B (3), and C (4), together with the known 7-oxodehydroabietic acid (5) were isolated and identified from the heartwood of Picea morrisonicola. The structures of 1—4 were determined on the basis of spectral data explanation. Compounds 2—4 possessed a rare 5-dehydro-18, 6-olide functionality. Compounds 1 and 2 were first isolated from natural source.View full abstractDownload PDF (59K) -
Kazuaki Shikii, Hiroko Seki, Kentaro Yamaguchi, Wannaporn Disadee, Tos ...2004 Volume 52 Issue 7 Pages 864-865
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSPolymer-supported (PS) reagents can be easily characterized using a cross polarization magic angle spinning method in solid state 13C-NMR. The technique was applied to the characterization of PS-dimethylimidazolidinone, analogue to potential heterogeneous dehydrating agent.View full abstractDownload PDF (53K) -
Ming-Jaw Don, Yeh-Jeng Huang, Ray-Ling Huang, Yun-Lian Lin2004 Volume 52 Issue 7 Pages 866-869
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSUsing the anti-hepatitis B virus (HBV)-producing cell line MS-G2 in vitro cultural system-guided screening was performed, and two new benzophenones, 2,6-dihydroxy-4-[(E)-5-hydroxy-3,7-dimethylocta-2,7-dienyloxy]benzophenone (1) and 2,6-dihydroxy-4-[(E)-7-hydroxy-3,7-dimethylocta-2-enyloxy]benzophenone (2), a new xanthone, hyperxanthone (3), a new bisanthraquinone glycoside, R-(−)-skyrin-6-O-β-D-xylopyranoside (4), and 2-caffeoyloxy-3-hydroxy-3-(3,4-dihydroxyphenyl)propyl alcohol (5), and 16 known compounds were isolated from the anti-HBV active fraction of the whole herbs of Hypericum sampsonii. Their structures were elucidated using spectroscopic methods, mainly 2D NMR and MS spectrometry. Circular dichroism was used to determine the stereochemistry of bisanthraquinone glycosides.View full abstractDownload PDF (79K) -
Ji Hye Byun, Ju Sun Kim, Sam Sik Kang, Kun Ho Son, Hyeun Wook Chang, H ...2004 Volume 52 Issue 7 Pages 870-873
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSFrom the roots of Sophora koreensis (Fabaceae), three new oleanene-type triterpene glycosides, echinosophorosides A1 (1) and B (2), and acetyl-subproside II (5), were isolated as their methyl esters, together with the four known ones sophoraflavoside I, kudzusaponin SA3, subproside II, and azukisaponin V. The structures of the new saponins were elucidated to be 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl kudzusapogenol A 22-O-α-L-arabinopyranoside (1), 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-(1→2)-β-D-glucuronopyranosyl abrisapogenol C 22-O-α-L-arabinopyranoside (2), and 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl kudzusapogenol A 22-O-acetate (5), respectively. It is noteworthy that two arabinopyranosyl moieties in the same molecule, echinosophoroside B (2), have different conformations. The conformation of the arabinopyranosyl moiety existing in the trisaccharide moiety was determined to be 1C4, whereas that of the arabinopyranosyl unit at C-22 was identified as 4C1.View full abstractDownload PDF (95K) -
Hyun Ok Yang, Sang Hee Kim, So-Hye Cho, Mi-Geum Kim, Ji-Young Seo, Jun ...2004 Volume 52 Issue 7 Pages 874-878
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSA mixture of monoacetyldiglycerides was newly isolated from the chloroform extract of antlers of Cervus nippon, guided by the hematopoietic stimulation of stem cells. The structures of monoacetyldiglycerides were determined by various spectroscopic methods: FAB MS, CID tandem MS, and 1D and 2D NMR. A mixture of at least nine inseparable sn-3-monoacetyldiglycerides was identified: 1 [C39H72O6 (C16 : 0/C18 : 1)], 2 [C39H72O6 (C18 : 1/C16 : 0)], 3 [C39H70O6 (C16 : 0/C18 : 2)], 4 [C39H70O6 (C18 : 2/C16 : 0)], 5 [C41H74O6 (C18 : 0/C18 : 2), 6 [C41H74O6 (C18 : 2/C18 : 0)], 7 [C41H74O6 (C18 : 1/C18 : 1)], 8 [C43H74O6 (C18 : 0/C20 : 4)], and 9 [C43H74O6 (C20 : 4/C18 : 0)]. Among these nine monoacetyldiglycerides in deer antlers, compound 3 was one of the major compounds and was efficiently synthesized from glycerol. Spectral data of synthetic monoacetyldiglyceride 3 were compared with the corresponding data for the mixture of natural monoacetyldiglycerides. The mixture of natural monoacetyldiglycerides from deer antlers showed potent activity on the hematopoiesis (stimulation index=1.40±0.05, p<0.02 at 1 μg/ml), and synthetic monoacetyldiglyceride 3 showed even better activity (stimulation index=1.54±0.12, p<0.001, at 1 μg/ml).View full abstractDownload PDF (493K) -
Phan Minh Giang, Phan Tong Son, Jung Joon Lee, Hideaki Otsuka2004 Volume 52 Issue 7 Pages 879-882
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSFrom the leaves of the endemic Vietnamese medicinal plant Croton tonkinensis GAGNEP. (Euphorbiaceae) the four new ent-kaurane-type diterpenoids ent-1α,14α-diacetoxy-7β-hydroxykaur-16-en-15-one (1), ent-1α,7β-diacetoxy-14α-hydroxykaur-16-en-15-one (2), ent-18-acetoxy-14α-hydroxykaur-16-en-15-one (3), and ent-(16S)-18-acetoxy-7β-hydroxykauran-15-one (4) were isolated. Their structures were elucidated by spectroscopic analyses.View full abstractDownload PDF (86K) -
Surat Laphookhieo, Chatchanok Karalai, Chanita Ponglimanont2004 Volume 52 Issue 7 Pages 883-885
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSA new sesquiterpene (1) and two new pentacyclic triterpenoid esters (2, 3) together with three known compounds (4—6) were isolated from the fruits of Rhizophora mucronata. Their structures were elucidated by analysis of their spectroscopic data. The new compounds were characterized as 3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,10-diene (mucronatone, 1), 3β-E-caffeoyltaraxerol (2) and 3β-Z-caffeoyltaraxerol (3).View full abstractDownload PDF (67K) -
Kazuko Yoshikawa, Mina Kuroboshi, Seiko Ahagon, Shigenobu Arihara2004 Volume 52 Issue 7 Pages 886-888
Published: 2004
Released on J-STAGE: July 10, 2004
JOURNAL FREE ACCESSThree novel triterpene esters, saponaceols A (1), B (2), and C (3) were isolated from the fruiting body of the fungus Tricholoma saponaceum, and their structures were elucidated on the basis of extensive NMR experiments. Saponaceol A (1) exhibited moderate inhibitory activity against HL-60 cells.View full abstractDownload PDF (72K)
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