Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 53 , Issue 1
Showing 1-36 articles out of 36 articles from the selected issue
Review
  • Seiichi Nakamura
    2005 Volume 53 Issue 1 Pages 1-10
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Zaragozic acids and squalestatins were documented by Merck, Glaxo, and Tokyo Noko University/Mitsubishi Kasei Corporation as part of a program aimed at identifying novel inhibitors of squalene synthase, as well as farnesyl transferase. These natural products have attracted considerable attention from numerous synthetic chemists because of their therapeutic potential and novel architecture. This review highlights our total syntheses of zaragozic acid C by two convergent strategies. The key steps in our first-generation synthesis involve 1) simultaneous creation of the C4 and C5 quaternary stereocenters through the Sn(OTf)2-promoted aldol coupling reaction between the α-keto ester and silyl ketene thioacetal derived from L- and D-tartaric acids, respectively; and 2) construction of the bicyclic core structure via acid-catalyzed internal ketalization under kinetically controlled conditions. The second-generation strategy relies on a tandem carbonyl ylide formation/1,3-dipolar cycloaddition approach and features elongation of the C1 alkyl side chain through an olefin cross-metathesis as well as high convergency and flexibility.
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Regular Articles
  • Chiou-Feng Chyu, Hsiu-Chuan Lin, Yueh-Hsiung Kuo
    2005 Volume 53 Issue 1 Pages 11-14
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Four new diterpenes, 3-oxosaprorthoquinone (1), 3-oxomicrostegiol (2), 3-oxoisotaxodione (3), and taiwaninal (4), together with two known compounds, 3-oxosapriparaquinone (5) and 6-dehydrohinokiol (6), were isolated from the roots of Taiwania cryptomerioides. The structures of 1—4 were principle elucidated based on spectral evidence.
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  • Ashraf Taha Khalil, Ya-Ching Shen, Jih-Hwa Guh, Shi-Yie Cheng
    2005 Volume 53 Issue 1 Pages 15-17
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Phytochemical investigation of Ixeris chinensis NAKAI (Asteraceae) has resulted in the isolation of a new guaianolide-type sesquiterpene lactone, ixerochinolide (1) as well as the related glucoside, ixerochinoside (2). In addition, the known guaianolides, 8β-hydroxy-3-oxo-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6-olide (8β-hydroxydehydrozaluzanin), 8β,15-dihydroxy-2-oxo-guaia-1(10),3,11(13)-trien-5α,6β,7αH-12,6-olide (lactucin), 3β,8α,10α-trihydroxy-guaia-4(15),11(13)-dien-1α,5α,6β,7αH-12,6-olide (10α-hydroxy-10,14-dihydro-desacylcynaropicrin) and 3β-D-glucopyranosyloxy-8β-(p-hydroxyphenylacetyloxy)-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6-olide (8-epicrepioside) were identified. The structures were determined on the basis of spectral analyses, especially 1- and 2D NMR. Compound 1 exhibited significant cytotoxicity against human PC-3 tumor cells.
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  • Satoru Watano, Takumi Okamoto, Yoshinobu Sato, Yoshito Ohnishi, Teruhi ...
    2005 Volume 53 Issue 1 Pages 18-21
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A novel multi-functional vertical high shear kneader has been developed and its performance in wet kneading has previously been reported [Watano et al., Chem. Pharm. Bull., 50(3), 341—345 (2002)]. In this study, scale-up of wet kneading in the novel vertical high shear kneader was conducted. Pharmaceutical excipients composed of lactose, cornstarch and micro-crystalline cellulose were used as powder samples. Kneading operations were conducted under various operating conditions and three different vessel scales. The dried pellets were then prepared by extruding the wet kneaded masses through a dome-type extruder and their drying by a fluidized bed. The physical properties such as strength and disintegration time of the dried pellets were evaluated. It was found that the properties of the dried pellets and their scale-up characteristics were well expressed by an agitation power per unit vessel volume and dimensionless Froude number.
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  • Eiko Toyota, Haruo Sekizaki, Yu-u Takahashi, Kunihiko Itoh, Kazutaka T ...
    2005 Volume 53 Issue 1 Pages 22-26
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Four series of Schiff base copper(II) and iron(III) chelates were synthesized from 4-formyl-3-hydroxybenzamidine or 3-formyl-4-hydroxybenzamidine and various L- or D-amino acids. Their inhibitory activities for bovine α-thrombin (abbreviated as thrombin) were determined. The most potent thrombin inhibitor in this series is copper(II) chelate (1g′) derived from 4-formyl-3-hydroxybenzamidine and D-Trp. Its Ki value, 2.7×10−8 M, is comparable to that of Argatroban (MD-805), which is a clinically used compound. The iron(III) chelates derived from 4-formyl-3-hydroxybenzamidine and hydrophobic L-amino acids (Val, Ile, Leu, Phe, Trp, Met) also exhibited higher inhibitory potency. It appears that coordination geometry composed of metal ion, amidino group, amino acid side chain is well accommodated to the thrombin active site. From the Ki values of Schiff base metal chelates for thrombin, the structure–activity relationships between the chelates and active site of thrombin were discussed.
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  • Kaname Hashizaki, Hiroyuki Taguchi, Chika Itoh, Hideki Sakai, Masahiko ...
    2005 Volume 53 Issue 1 Pages 27-31
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Poly(ethylene glycol)-grafted liposomes (PEG-liposomes) were prepared from dipalmitoylphosphatidylcholine (DPPC) with various amounts of distearoyl-N-monomethoxy poly(ethylene glycol)-succinyl-phosphatidylethanolamines (DSPE-PEG) with PEG molecular weights of 1000, 2000, 3000 and 5000. The effects of DSPE-PEG concentration on the permeability of PEG-liposomes were investigated using carboxyfluorescein (CF). In the gel state, the CF leakage from PEG-liposomes was decreased with increasing mole fractions of DSPE-PEG for all PEG molecular weights. In the liquid-crystalline state, the CF leakage from PEG-liposomes containing DSPE-PEG1000 gradually increased with increasing mole fractions of DSPE-PEG, while that of PEG-liposomes whose molecular weight in PEG units was above 2000 rapidly decreased by the addition of DSPE-PEG. Furthermore, no effect of PEG molecular weight on CF leakage was observed. The relationship between the fluorescence polarization of 1,6-diphenyl-1,3,5-hexatriene (DPH) (or 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH)) and the mole fraction of DSPE-PEG for PEG-liposomes was also investigated. No significant changes in fluorescence polarization of DPH for liposomal bilayer membranes was observed in the gel and liquid-crystalline states due to the addition of DSPE-PEG, while that of TMA-DPH was decreased compared with that of liposomes without DSPE-PEG in both states.
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  • Ya-Ching Shen, Ching-Yeu Chen, Pei-Wen Hsieh, Chang-Yih Duh, Yat-Min L ...
    2005 Volume 53 Issue 1 Pages 32-36
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A series of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives have been synthesized and evaluated for antitumor activity against murine P-388 and human tumor cell lines, KB-16, A-549 and HT-29. All of the compounds prepared, except for 19, showed significant cytotoxicity. Among them, compound 29 exhibited the most potent activity against all tested tumor cell lines. There was an apparent lack of correlation regarding cytotoxicity between 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carbolines. This study is the first to discover compound 29 as a potential lead for the development of future anticancer agents. The mode of inhibition for compound 29 was proposed.
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  • Hirokazu Takahashi, Richer Chen, Hirokazu Okamoto, Kazumi Danjo
    2005 Volume 53 Issue 1 Pages 37-41
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    In this study matrices were prepared from particles of poorly water-soluble drugs such as acetaminophen (Act) to determine the drug release rate from these matrix particles. The matrix particles were prepared by incorporating drugs into chitosan powder (Cht, carrier) using a spray-drying method. The formation of composite particles was confirmed by scanning electron microscopic (SEM) analysis. The matrix particles prepared by spray-drying were spherical with a smooth surface. The crystallinity of acetaminophen in the composite particles was evaluated by powder X-ray diffraction and differential scanning calorimetry (DSC). The degree of crystallinity of acetaminophen in the matrix particles decreased with a reduction in the weight ratio of acetaminophen relative to the carrier. These results indicate that a solid dispersion of acetaminophen in chitosan forms matrix particles. The interaction between acetaminophen and chitosan was also investigated by FT-IR analysis. FT-IR spectroscopy of the acetaminophen solid dispersion suggested that the carbonyl group of acetaminophen and the amino group of chitosan formed a hydrogen bond. There were some differences at pH levels of 1.2 and 6.8 in the release of acetaminophen from the physical mixture compared to the matrix particles. At pH 1.2, the release from the matrix particles (Act : Cht=1 : 5) was more sustained than from the physical mixtures. The 70% release time, T70, of acetaminophen from the matrix particles (Act : Cht=1 : 5) increased in pH 1.2 fluid by about 9-fold and in pH 6.8 fluid by about 5-fold compared to crystalline acetaminophen. These results suggest that matrix particles prepared by spray-drying are useful as a sustained release preparation.
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  • Isao Ohtsuka, Shoko Yokoyama
    2005 Volume 53 Issue 1 Pages 42-47
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    The penetration of bovine serum albumin (BSA) into dipalmitoylphosphatidylglycerol (DPPG) monolayers was observed using atomic force microscopy (AFM) and surface pressure measurements. The effects of surface pressure, amount of BSA and the addition of ganglioside GM1 (GM1) were investigated. The surface pressure of the DPPG monolayer was increased by the penetration of BSA, and the increase in surface pressure was greater in the liquid-expanded film than that in the liquid-condensed film. The AFM images indicated that BSA penetrated into the DPPG monolayer. The amount of BSA that penetrated into the DPPG monolayer increased with time and with the amount of BSA added. On the contrary, the AFM image showed that BSA penetration into the mixed DPPG/GM1 (9 : 1) monolayer scarcely occurred. GM1 inhibited the penetration of BSA into the DPPG monolayer.
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  • Masafumi Kikuchi, Masao Kikuchi
    2005 Volume 53 Issue 1 Pages 48-51
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alco-hol glycoside, 3-butenyl 6′-O-α-L-arabinopyranosyl-β-D-glucopyranoside (3), and a new lignan glycoside, 7R,7′R,8S,8′S-(+)-neo-olivil-4-O-β-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica MAKINO. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.
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  • Hiroko Nakagawa, Koh-ichi Yamada
    2005 Volume 53 Issue 1 Pages 52-55
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    The circular dichroism (CD) spectra of three types of (L)phosphatidylcholine (PC) vesicles in aqueous solution showed differences in the sign and intensity of the Cotton effect compared with those of monomers in ethanol, indicating the existence of chiral environments in these vesicles. From the temperature dependence of CD intensities, the main phase transition temperatures between gel (Gel) and liquid-crystalline (LC) phases of the vesicles were estimated to be 40, 23, and 55 °C for dipalmitoyl PC, dimyristoyl PC and distearoyl PC, respectively. Furthermore, both low-fluidity Gel and high-fluidity LC phases recognized the chirality of incorporated 2-hydroxymethyl[5]thiaheterohelicene (5HM) with a helical structure, which undergoes a rapid racemization owing to a weak repulsion between the terminal hydrogen atoms. The ability for chiral recognition was evaluated using thermodynamic parameters for the equilibrium between P and M enantiomers of 5HM in the vesicles; the Gel phase manifested a higher recognition ability than the LC phase.
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  • Pei-Lin Wu, Tian-Shung Wu, Cai-Xia He, Chia-Hao Su, Kuo-Hsiung Lee
    2005 Volume 53 Issue 1 Pages 56-59
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Five new compounds, hibicuslide A (1), hibicuslide B (2), hibicuslide C (3), hibicutaiwanin (4), hibicusin (5), and fifty-one known compounds have been isolated from the stems of Hibiscus taiwanensis. The structures of these compounds were determined by spectroscopic and chemical transformation methods. Among them, mansonone H (19) and uncarinic acid A (30) inhibited HIV replication in H9 lymphocyte cells. The 9,9′-O-feruloyl-(−)-secoisolaricinresinol (12), myriceric acid C (29), and uncarinic acid A (30) showed cytotoxic activity against human lung carcinoma and breast carcinoma.
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  • Haruki Sashida, Kazuo Ohyanagi
    2005 Volume 53 Issue 1 Pages 60-63
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    While the solvent-free reactions of the 2-benzoselenopyrylium salts (9) with methyl- or phenylhydrazine afforded the 1-hydrazino-1H-isoselenochromenes (11, 12), the treatment of the salts (9) with anhydrous hydrazine in dry acetonitrile resulted in a ring transformation to give the 5H-2,3-benzodiazepines (13) in one-pot under mild conditions in moderate yields.
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  • Zafar Saeed Saify, Nousheen Mushtaq, Khalid Mohammed Khan, Shahnaz Per ...
    2005 Volume 53 Issue 1 Pages 64-66
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A new series of 4-(4′-chlorophenyl)-4-hydroxypiperidine derivatives (2—5), substituted at nitrogen, were synthesized and tested as potential analgesic compounds as well as evaluated for their effect on hypotensive activity. Results showed that all the derivatives exhibit significant analgesic activity in male Wistar rats at a dose of 50 mg/kg of body weight after intramuscular injection, when tested by thermal stimuli (tail flick test). Pethidine was used as reference drug. Compounds 2, 3 and 5 produced reduction in blood pressure in normotensive rat.
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  • Shaozhong Wang, Liya Cao, Haijian Shi, Yanmei Dong, Jianwei Sun, Yuefe ...
    2005 Volume 53 Issue 1 Pages 67-71
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A novel and practical preparation of 2-pyridone-containing tricyclic alkaloid derivatives was developed. By regioselective intramolecular N- and C-acylation of 2-(4-aryl-2-pyridon-6-yl)benzoic acid, a pair of structural isomers 2-aryl pyrido[2,1-a]isoindole-4,6-diones and 4-aryl 1-methyl-1H-indeno[1,2-b]-pyridine-2,5-diones, as potential inhibitors of tumor cell proliferation, were prepared respectively.
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  • Yoshiyasu Fukuyama, Miwa Kubo, Hiroyuki Minami, Hiroaki Yuasa, Asami M ...
    2005 Volume 53 Issue 1 Pages 72-80
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Nine new diterpenes, neovibsanin D (1), 7-epi-neovibsanin D (2), 15-O-methylneovibsanin F (3), 14-epi-15-O-methylneovibsanin F (4), 15-O-methyl-18-oxoneovibsanin F (5), 2-O-methylneovibsanin H (6), 2-O-methylneovibsanin I (7), neovibsanin G (8), and 14-epi-neovibsanin G (9), were isolated from a methanol extract of the leaves of Viburnum awabuki. Their structures were elucidated to be uniquely rearranged vibsane-type diterpenes by spectroscopic analyses and comparison of NMR data with those of previously reported vibsane-type diterpenes. In addition, irradiation of vibsanin B (12) in methanol with a high-pressure Hg lump led to the direct formation of neovibsanins A (14) and B (15). These results gave a clue to understanding of the biogenetic interconversion of 11-membered vibsanins into neovibsanins.
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  • Yasushi Arakawa, Manabu Tajima, Yukimi Arakawa, Shigeyuki Yoshifuji
    2005 Volume 53 Issue 1 Pages 81-85
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Diels–Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new 4-amino-1,2,3-cyclohexanetricarboxylic acids and 4-amino-1,3-cyclohexanedicarboxylic acids.
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Notes
  • Sher Bahadar Khan, Azhar-ul-haq, Nighat Afza, Abdul Malik, Mahmud Tar ...
    2005 Volume 53 Issue 1 Pages 86-89
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Long-chain esters 1 and 2 have been isolated from the chloroform-soluble fraction of Amberboa ramosa and their structures assigned to be methyl 2β(2S)-hydroxyl-7(E)-tritriacontenoate (1) and methyl 2β(2S)-O-β-D-galactopyranosyl-7(E)-tetratriacontenoate (2). In addition, tricontane (3) and apigenin (4) are also reported for the first time from this species. The structures were assigned on the basis of 1D and 2D NMR techniques. Compounds 1 and 2 showed strong to moderate inhibitory activity against tyrosinase.
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  • Kazuaki Ito, Kayo Nagase, Naoya Morohashi, Yoshihiro Ohba
    2005 Volume 53 Issue 1 Pages 90-94
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    The binding properties of dipeptides possessing aromatic residues towards quaternary ammonium ions have been investigated by 1H-NMR spectroscopy. The intermolecular hydrogen bonding between exchangeable protons (OH and NH) of aromatic residues of dipeptides and the counter anion of ammonium ion is the primary force. After the formation of the intermolecular hydrogen bonding, two aromatic residues of dipeptides can provide π-base cavity to interact with the quaternary ammonium moiety.
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  • Parinuch Chumkaew, Shigeru Kato, Kan Chantrapromma
    2005 Volume 53 Issue 1 Pages 95-96
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A new lupane caffeoyl ester (1), 3-(Z)-caffeoyllupeol, together with five known triterpenoids, lupeol caffeate (2), 3-(Z)-coumaroyllupeol (3), dioslupecin A (4), lupeol (5), and lupenone (6), were isolated from the fruits of Bruguiera parviflora. Their structures were elucidated by spectroscopic methods. Compound 1 exhibited antimalarial activity with an EC50 value of 8.6 μg/ml, but compound 2 was inactive.
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  • Sang-Yong Park, Hyun-Sik Choi, Chang-Soo Yook, Toshihiro Nohara
    2005 Volume 53 Issue 1 Pages 97-99
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A new lupane-type saponin, named acankoreoside E (1), was isolated from the methanol extract of the leaves of Acanthopanax koreanum, and its structure was established through chemical and spectroscopic analyses as (20S) 3α-hydroxy-30-oxolupan-23,28-dioic acid 28-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester.
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  • Shigeo Sugiyama, Satoshi Arai, Matsuri Kiriyama, Keitaro Ishii
    2005 Volume 53 Issue 1 Pages 100-102
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).
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  • Young Lim Kim, Young-Won Chin, Jinwoong Kim
    2005 Volume 53 Issue 1 Pages 103-104
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Two new neolignans (1, 2) were isolated from the aerial parts of Rodgersia podophylla, along with four known neolignans, and their structures were elucidated using spectral experiments and comparison with literature data.
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  • Hye Kyong Kim, Young Hae Choi, Cornelis Erkelens, Alfons W. M. Lefeber ...
    2005 Volume 53 Issue 1 Pages 105-109
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    The metabolomic analysis of Ephedra species was performed using 1H-NMR spectroscopy and multivariate data analysis. A broad range of metabolites could be detected by 1H-NMR spectroscopy without any chromatographic separation. The principal component analysis used to reduce the huge data set obtained from the 1H-NMR spectra of the plant extracts clearly discriminated three different Ephedra species. The major differences in Ephedra sinica, Ephedra intermedia and Ephedra distachya var. distachya were found to be due to benzoic acid analogues in the aqueous fraction and ephedrine-type alkaloids in the organic fraction. Based on this metabolomic recognition, one of nine commercial Ephedra materials evaluated was shown to be a mixture of Ephedra species. This method will be a useful tool for chemotaxonomic analysis and authentification of Ephedra species including quality control of plant materials.
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  • JianShuang Jiang, ZiMing Feng, YingHong Wang, PeiCheng Zhang
    2005 Volume 53 Issue 1 Pages 110-113
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Three new phenolics, (1S,2R)-1-(4′-O-β-D-glucopyranosyl-3′-methoxyphenyl)-2-(4″-hydroxy-3″-methoxyphenyl)-1,3-propanediol, symplolignanoside A, and 3,4-dimethoxyphenol β-D-apiofuranosyl(1→6)-β-D-glucopyranoside, along with eight known compounds were isolated from the roots of Symplocos caudata WALL. Their structures were elucidated by spectroscopic and chemical methods.
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  • Nguyen Tien Dat, Xing Fu Cai, Quanghai Shen, Im Seon Lee, Young Ho Kim
    2005 Volume 53 Issue 1 Pages 114-117
    Published: 2005
    Released: January 01, 2005
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    Two new compounds were isolated from the stem and twigs of Ribes fasciculatum var. chinense and their structures were identified to be threo-(7S,8R)-1-(4-hydroxyphenyl)-2-[4-(E)-propenylphenoxy]-propan-1-ol (1), and 5,4′-dihydroxy-7-methoxyflavone-3-O-[α-L-rhamnopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→6)-O-β-D-glucopyranoside] (2). With nine other known components, they were tested on inhibitory activity against nuclear factor of activated T cells (NFAT) transcription factor. Compound 1 showed a potent inhibitory activity (IC50=15.6 μM), while compounds 4, 5 and 9 showed moderate inhibitory activity (IC50 22.4, 24.5 and 25.7 μM, respectively).
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  • Thanh Nguyen Le, Won-Jea Cho
    2005 Volume 53 Issue 1 Pages 118-120
    Published: 2005
    Released: January 01, 2005
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    Oxychelerythrine, benzo[c]phenanthridine alkaloid, was synthesized from easily available starting toluamide 5 and benzonitrile 6 using toluamide-benzonitrile cycloaddition reaction in 6 steps.
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  • Tenji Konishi, Takao Konoshima, Akihiro Daikonya, Susumu Kitanaka
    2005 Volume 53 Issue 1 Pages 121-124
    Published: 2005
    Released: January 01, 2005
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    From a MeOH extract of the aerial part of Piper futokadsura, the tetrahydrofuran lignans, futokadsurin A [(7S,8S,7′S,8′R)-3,4,3′-trimethoxy-4′-hydroxy-7,7′-epoxylignan], futokadsurin B [(7R,8R,7′R,8′S)-3,4-dimethoxy-3′,4′-methylenedioxy-7,7′-epoxylignan], and futokadsurin C [(7R,8R,7′S,8′S)-3,4-methylenedioxy-3′,4′-dimethoxy-7,7′-epoxylignan] were isolated, together with nine known neolignans. In addition, L-tryptophan, pellitorine, phytol, elemicin, and 1,2,4-trimethoxyphenyl-5-aldehyde were isolated. The structures of the new compounds were elucidated using spectroscopic methods. These lignans inhibited nitric oxide production by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide and interferon-γ.
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  • Yoshiyasu Fukuyama, Yuka Minoshima, Yoshiko Kishimoto, Ih-Sheng Chen, ...
    2005 Volume 53 Issue 1 Pages 125-127
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Four new iridoid aldehydes bearing (E)- or (Z)-p-coumaroyl group, luzonial A (1), luzonial B (2), luzonidial A (3), and luzonidial B (4), were isolated from a methanol extract of the dried leaves of Viburnum luzonicum collected in Kaoshiung, Taiwan and their structures were elucidated by analysis of spectroscopic data. Compounds 1—3 exhibited moderate inhibitory activity against HeLa S3 cancer cells.
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  • Yu-Chi Lin, Yeh-Li Huang, Ashraf Taha Khalil, Meng-Hsien Chen, Ya-Chin ...
    2005 Volume 53 Issue 1 Pages 128-130
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Chemical investigation of the gorgonian coral Junceella juncea collected in Taiwan has resulted in the isolation of the two novel briarane-type diterpenoid compounds, juncenolides F (1) and G (2). The structures were determined on the basis of spectral studies, especially 1D and 2D NMR.
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  • Shigeki Sano, Eiko Kujime, Yuka Takemoto, Motoo Shiro, Yoshimitsu Naga ...
    2005 Volume 53 Issue 1 Pages 131-134
    Published: 2005
    Released: January 01, 2005
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    Novel chiral phosphonoacetates bearing a stereogenic phosphorus atom were successfully synthesized by enzyme-catalyzed kinetic resolution of racemic phosphonoacetates.
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  • Biswanath Das, Gurram Mahender, Yerra Koteswara Rao, Anabathula Prabha ...
    2005 Volume 53 Issue 1 Pages 135-136
    Published: 2005
    Released: January 01, 2005
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    Chemical investigation on the constituents of the cones of Cycas beddomei has resulted in the isolation of a new biflavonoid, 2,3-dihydro-4′′′-O-methyl amentoflavone, along with 2,3,2″,3″-tetrahydro hinokiflavone, 2,3,2″,3″-tetrahydro amentoflavone, 2,3-dihydro amentoflavone. The last two compounds were not reported earlier from this plant. The structure of the new compound was established by detailed analysis of its spectral (mainly 1D and 2D NMR) data.
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  • Li-Yan Wang, Tomoko Unehara, Susumu Kitanaka
    2005 Volume 53 Issue 1 Pages 137-139
    Published: 2005
    Released: January 01, 2005
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    In our investigation of in vitro anti-allergic screening of medicinal herbal extracts, the ethyl acetate extract of the root of Wikstroemia indica was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ) activated murine macrophage-like cell line, RAW 264.7. Fractionation of the active extract led to the isolation of one new guaiane type sesquiterpene, indicanone (1), and two known biflavonoids, sikokianin B (2) and sikokianin C (3). 1 inhibited NO production with IC50 values at 9.3 μM and also inhibit the inducible nitric oxide synhase (iNOS) gene expression. This is the first report of NO production inhibitory activity of Wikstroemia indica and supports the pharmacological use of it, which has been employed as an herbal medicine for the treatment of inflammation.
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  • Makoto Hashimoto, Tomoko Komano, Kensuke Nabeta, Yasumaru Hatanaka
    2005 Volume 53 Issue 1 Pages 140-142
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Summary A convenient procedure for the synthesis of (E)- and (Z)-β-bromostyrene containing trifluoromethyldiazirine is described, which involves the stereoselective reduction of the corresponding trifluoromethyldiazirinyl β,β-dibromostyrene without damaging the photophor. The synthetic route easily introduced deuterium, which can be utilized for the detection of a photolabeled component by MS spectrometry, after construction of a trifluoromethyldiazirinyl skeleton.
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  • Tatjana Mateović-Rojnik, Rok Frlan, Marija Bogataj, Peter Bukove ...
    2005 Volume 53 Issue 1 Pages 143-146
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    Eudragit RS 100 microspheres containing ketoprofen as a model drug were prepared by the solvent evaporation method using an acetone/liquid paraffin solvent system. The influence of various preparation temperatures: 10, 25, 35, and 40 °C, on particle size and morphology, drug content and release kinetics, and drug crystal state was evaluated. With increasing temperature, microsphere average size was found to increase and particle size distribution to widen significantly. At 10 °C particles of irregular shape are formed, whereas higher temperatures gradually improve the sphericity of microspheres. As can be seen from SEM photographs, particle surface roughness decreases as preparation temperature increases. It was found that temperature had no effect either on ketoprofen microencapsulation efficiency or on its crystal state, but it does influence emulsion-stabilizer incorporation. Ketoprofen forms solid solution in Eudragit matrix and maintains amorphous state for significant period of time. Drug release rates from microspheres correlated with microspheres' surface roughness and to a lesser extent with particle size.
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  • Shigehiko Takegami, Keisuke Kitamura, Tatsuya Kitade, Miwa Takashima, ...
    2005 Volume 53 Issue 1 Pages 147-150
    Published: 2005
    Released: January 01, 2005
    JOURNAL FREE ACCESS
    To assess the affinity of psychotropic phenothiazine drugs, triflupromazine (TFZ) and chlorpromazine (CPZ), for the membranes of central nervous system and the other organs in the body, the partition coefficients (Kps) of these drugs to phosphatidylcholine (PC)–phosphatidylserine (PS) and PC–phosphatidylethanolamine (PE) small and large unilamellar vesicles (SUV, LUV) were examined by a second-derivative spectrophotometric method, since PS is abundantly contained in the membranes of the central nervous system and PE is distributed widely in the membranes of the organs in the body. Size and preparation methods of the vesicles did not affect the Kp values at each aminophospholipid content suggesting that the partition of the phenothiazine drugs was not affected by the structural differences in the vesicles such as their curvature or asymmetric distribution of the phospholipids between the outer and inner layers of the bilayer membranes. However, the Kp values of both drugs increased remarkably according to the PS content in the bilayer membranes, i.e., the Kp values for the vesicles of 30 mol% PS content were about 3 times of that for the vesicles of PC alone, while both Kp values slightly reduced with the increase in the content of PE in the bilayer membranes of PC–PE vesicles. The results indicate that both drugs have higher affinity for the PC–PS bilayer membranes than for the PC and PC–PE membranes, which can offer an evidence for the fact that TFZ and CPZ are predominantly distributed and accumulated in the brain and nerve cell membranes that contain PS abundantly.
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