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Volume 41, Issue 3
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Yoshio SASAKI, Tatsuya TAKAGI, Hideko KAWAKI1993 Volume 41 Issue 3 Pages 415-423
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRational estimation of the descriptor σ S°, representing the dispersion and repulsion energies in the van der Waals interaction for both aliphatic and aromatic moieties, enabled us to present the descriptors of several important medicinals now available. In this work, the fundamental rule for the estimation of the descriptor for a substrate having a variety of binding modes and the correction value ΔS° necessary for aliphatic heterocycle formation are confirmed, and the descriptors for several important moieties are established according to the concept of quantitative structure-activity relationship analogy. Furthermore, several kinds of herbicides, antiinflammatory agents, hypocholesterolemics, analogesics, sympathetic stimulants, and antipsychotics are concerned in this work.View full abstractDownload PDF (946K) -
Kentaro YAMAGUCHI1993 Volume 41 Issue 3 Pages 424-429
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fully automatic procedure has been devised for crystal structure analysis by X-ray crystallography. Automatic decisions at each critical point of the analysis, at which user intervention used to be required, are provided based on empirical considerations. The new procedure, named FACE (Fully Automatic Struture Elucidation), simply refins the intense peaks using two-step weighted Fourier (WTF) calculations following phase determination. The molecular recognition based on the interpretation of electron-density maps is not necessary in this procesure. It is able to solve structures without any user intervention; the user simply inputs "FASE" to carry out this procedure. The complete structure is solved and displayed in most cases. This procedure has been applied to 137 crystals of organic compounds and 112 chemically significant structures were derived. The R values refined without any missing atom using isotropic refinement normally lie in the range of 0.15-0.30, which are acceptable values in such a rough stage (all non-hydrogen atoms are assigned as carbon). These results usually reached to the final structure, including hydrogen atoms with R values around 0.05, by further anisotropic refinement using appropriate methods.View full abstractDownload PDF (825K) -
Nobuo OKABE, Misa HOKAZE1993 Volume 41 Issue 3 Pages 430-432
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fluorescence method was used to investigate the effect of inorganic anions, SCN-, I-, ClO-4 and Br- on the binding of thyroxine (T4) by bovine serum albumin (BSA). The apparent binding constants were evaluated in 0.1 M sodium phosphate buffer, pH 7.4 at 25°C containing various concentrations of the anions up to 0.15 M. Their values decreased at high anion concentrations. The effectiveness of anions in reducing T4 binding was in the following order : SCN- > I- > ClO-4 > Br- . Thermodynamic parameters determined in the presence of 0.1 M SCN- suggested that the hydrophobic interaction between T4 and BSA could be reduced by these inorganic anions.View full abstractDownload PDF (501K) -
Toshimasa ISHIDA, Hiroomi NAGATA, Yasuko IN, Mitsunobu DOI, Masatoshi ...1993 Volume 41 Issue 3 Pages 433-438
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the difference between the indole-picric acid interaction modes formed in the L- and DL-tryptophan-picric acid complex crystals, the crystal structure of the former complex was analysed by the X-ray diffraction method and the interaction geometry observed was compared with that of the latter complex crystal already analysed. Two crystallographically independent charge-transfer interaction pairs were formed in the crystal structure and formed discrete stacking layers consisting of tryptophan and picric acid molecules. The indole and pricric acid planes were parallely stacked with an interplanar spacing near to 3.4 Å in both pairs. This reflects the structural feature necessary for the charge-transfer interection characterized by the red coloration of complex crystal. Three kinds of indole-picric acid stacking geometries observed were similar with one another, and one of them was almost the same as that in the DL-tryptophan-picric acid complex crystal. This indicates that the observed indole-picric acid interaction mode reflects an intrinsic feature and is not significantly affected by the different chirality of the tryptophan side chain and crystal environment.View full abstractDownload PDF (825K) -
Convenient Synthesis of 2, 4-Cyclohexadien-1-ones by Regioselective Methylthiomethylation of PhenolsSadamu KATAYAMA, Toshio WATANABE, Masashige YAMAUCHI1993 Volume 41 Issue 3 Pages 439-444
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA convenient synthesis of a variety of 2, 4-cyclohexadien-1-ones 3-7 is described. Reaction of various phenols 2 having appropriate substituents with an excess of S, S-dimethylsuccinmidosulfonium chloride (Corey-Kim reagent, 1)in the presence of triethylamine proceeded with regioselective methylthiomethylation to give methylthiomethyl, bis(methylthiomethyl), or tris(methylthiomethyl)-2, 4-cyclohexadien-1-ones 3-7 in satisfactory yields.View full abstractDownload PDF (1007K) -
Nobuharu KATO, Masanobu FUJITA, Ken-ichi FUJIMURA, Yoichi KAWASHIMA, Y ...1993 Volume 41 Issue 3 Pages 445-452
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCitrusinine-I (1), a naturally occurring acridone alkaloid with potent anitiviral activity, was synthesized for the first time, via a route involving Ulmann reaction, cyclization, and selective demethylation at the 1-position with boron trifluoride etherate and lithium bromide. 1, 5, 6-Trihydroxy-3-methoxy-9(10H)-acridone (2a) and 1, 5, 6-trihydroxy-3-methoxy-10-methyl-9(10H)-acridone (2b) were also synthesized.View full abstractDownload PDF (1218K) -
Tohru SAITO, Miyoko MURAKAMI, Tadaaki INADA, Hiromi HAYASHIBARA, Tozo ...1993 Volume 41 Issue 3 Pages 453-457
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 9-ethy-1-(2-hydroxythyl)adenide hydrobromide (1a) in boiling N, N-dimethylformamide (DMF) with an excess of thiourea for 7 h or with an excess of ammonium thiocyanate for 3 h provided 3-ethyl-7, 8-dihydro-3H-imidazo[2, 1-i]purinium thiocyanate (8) in 51% or 58% yield, respectively. On treatment with an excess of triphenyl phosphite in boiling DMF for 20 min, 1 a underwent a similar cyclization to from the same tricycle, which was isolated in 81% yield (from 1 a)in the form of the perchlorate salt (12). A similar treatment of 1 a with triethyl phosphite furnished the 9-ethyl analogue (15) in 83% yield. Conversion of 12 into the free base and oxidation of latter with active MnO2 in boiling CH2Cl2 for 16 h gave 3-ethyl 3-ethyl-3H-imidazo[2, 1-i]purine (13) (66% overall yield from 12), which was identical with a sample synthesized from 9-ethyladenine (9) and chloroacetaldehyde according to the general N6, 1-etheno bridgeing procedure. On treatment with methanolic ammonia at room temperature, the tricycle 15 afforded 9-ethyl-N6-[2-(ethylamino)ethyl]adenine hydrobromide (26) in 79% yield. Mechanisms are proposed for the above intramolecular cyclizations of 1 a caused by the S- and P-atom nucleophiles.View full abstractDownload PDF (866K) -
Kazuyuki MIYASHITA, Koji YONEDA, Tomohiro AKIYAMA, Yasuo KOGA, Ryozo T ...1993 Volume 41 Issue 3 Pages 458-464
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe total synthesis of (±)-dehalogenonidifocene (3), a potential key intermediate for the total synthesis of(±)-nidifocene (1), is described, in which the key steps are the construction of the basic tricyclic skeleton and the regioselective introduction of the double bond. Construction of the tricyclic skeleton could be achieved by the intramolecular Michael-type addition of the hydroxyl group of the exo-methylene compound 6, and the reduction of the conjugated diene moiety of 9 with ytterbium in liqud ammonia afforded the target molecule in a regioselective manner.View full abstractDownload PDF (1063K) -
Kazuyuki MIYASHITA, Koji YONEDA, Tomohiro AKIYAMA, Yasuo KOGA, Masahir ...1993 Volume 41 Issue 3 Pages 465-470
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo stereoisomers, 6 and 15, of nidifocene (1) were synthesized in a regio- and stereoselective manner by means of direct addition of "BrCl", generated from N-bromosuccinimide and ammonium chloride, to dehalogenonidifocene (3) and by means of displacement of the hydroxyl group of the chlorohydrin 21, stereoselectively prepared from 3, with bromine.View full abstractDownload PDF (958K) -
Takehiro SANO, Hiroshi ENOMOTO, Yasuko KUREBAYASHI, Yoshie HORIGUCHI, ...1993 Volume 41 Issue 3 Pages 471-477
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photocycloaddition reaction of 4, 5-diethoxycarbonyl-1H-pyrrole-2, 3-dione 4 to acyclic olefins proceeded in a regioselective manner to give two head to tail adducts, the exo- (5) and endo-isomers (6). The stereochemistry of the 7-substituents of the adducts changed depeding on the electronic properties of olefins. Olefins with O-substituents(ethoxyethylene, acetoxyethylene) stereoselectively gave the endo-adducs (6d, e). Olefins with phenyl and ethyl substituents, styrene and 1-butene, gave a mexture of the exo- (5a, b) and endo-adducts (6a, b) with exo-preference.Butadiene gave the exo- (5b) and endo-adduct (6b) with slight excess of the latter. These stereochemical results are in good accordance with the predictions obtained by the sterep-selection rule of enone-olefin photocycloaddition.View full abstractDownload PDF (1143K) -
Takao SAKAMOTO, Daishi UCHIYAMA, Yoshinori KONDO, Hiroshi YAMANAKA1993 Volume 41 Issue 3 Pages 478-480
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene gave 3, 5-disubstituted 4-(trimethylstannyl)isoxazoles almost regioselectively. The regioselectivity of the cycloaddition reaction is interpreted by application of the frontier-electron theory.View full abstractDownload PDF (599K) -
Yutaka OZAKI, Ayako KUBO, Sang-Won KIM1993 Volume 41 Issue 3 Pages 481-483
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA [3C + 3C] annelation using 1, 1-bis(ethulthio)-2-propanone was applied to a new synthesis of the aporphine alkaloids. Condensation of the ketone with the Mannich base gave two isomeric cyclohexenones, which were converted into the aporphine framework by aromatization. (±)-Glaucine and (±)-nantenine were prepared by employing this new aromatic synthesis.View full abstractDownload PDF (517K) -
Shinji FUSHIYA, Qian-Qun GU, Keiko ISHIKAWA, Shinji FUNAYAMA, Shigeo N ...1993 Volume 41 Issue 3 Pages 484-486
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn antagonist of NMDA-sensitive glutamate receptors in rat brain membrane and rat spinal motoneurones was isolated from Amanita pantherina and ideneified as a diastereoisomeric mixture of 2-amino-3-(1, 2-dicarboxyethylthi)propanoic acids. The mixture was separated and the absolute configurations of the components were determined as (2R), (1'R) and (2R), (1'S), by analysis of the properties.View full abstractDownload PDF (585K) -
Shigetoshi KADOTA, Satoshi TERASHIMA, Purusotam BASNET, Tohru KIKUCHI, ...1993 Volume 41 Issue 3 Pages 487-490
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPalbinone, a novel terpenoid isolated from the roots of Paeonia albiflora, showed a strong inhibitory activity on the reduced from of nicotinamide adenine dinucleotide phosphate (NADPH)-linked 3α-hydroxysteroid dehydrogenase(3α-HSD) of rat liver cytosol. The structures of palbinone and a known compound, paeonilactone-B isolated from the active fraction of this plant were determined by the use of 2D NMR techniques (1H-1H COSY, 1H-13C COSY, 1H-13C-long-range COSY, and HMBC).View full abstractDownload PDF (630K) -
Hong-Min LIU, Yoshiyuki SATO, Yoshisuke TSUDA1993 Volume 41 Issue 3 Pages 491-501
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSixteen oxo derivatives of methyl D-hexopyranosides with various regio- and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of pfrtially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pryidine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.View full abstractDownload PDF (1649K) -
Takaki KOIDE, Hiromi ITOH, Akira OTAKA, Hiroyuki YASUI, Masataka KUROD ...1993 Volume 41 Issue 3 Pages 502-506
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine [Fmoc-Sec(MBzl)-OH] was synthesized from selenocystine and successfully applied to Fmoc-based solid-phase peptide synthesis. The stability and the deprotection conditions of the Se-MBzl group were examined. The diselenide bond of a pepride was directly and effectively established between Sec(MBzl) residues by treatment with iodene or the dimethyl sulfoxide-trifluoroacetic acid system. Reduction kinetics of didelenide and disulfide in model peptides by reduced glutathione were also studied comparatively.View full abstractDownload PDF (814K) -
Kazuhiko TAKE, Kazuo OKUMURA, Kazunori TSUBAKI, Takao TERAI, Youichi S ...1993 Volume 41 Issue 3 Pages 507-515
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of pyrrolidine derivatives were synthesized and examined for inhibitory activity on detrusor contraction in vivo. Among those compounds, 5, 5-dimethyl-2(2, 2-diphenylethyl)-3-isopropylidenepyrrolidine hydrochloride(41·HCl), 2-(2, 2-di(4-fluorophenyl)ethylene)-5, 5-dimethyl-3-isopropylidenepyrrolidine hydrochloride (42·HCl), (+)-5, 5-dimethyl-2-(N, N-diphenylaminomethyl)-3-isopropylidenepyrrolidine hydrochloride (+)-(43a·HCl), (-)-5, 5-di-methyl-2-(N, N-diphenylaminomethyl)-3-isopropylidenepyrrolidine hydrochloride (-)-(43a·HCl), and 2-(N, N-di(4-fluorophenyl)aminomethyl)-5, 5-dimethyl-3-isopropylidenepyrrolidine methanesulfonate (43b·MsOH) showed stronger inhibitory activity on detrusor contraction than terodiline.View full abstractDownload PDF (1246K) -
Tokumi MARUYAMA, Yasuaki HANAI, Yoshiko SATO, Robert SNOECK, Graciela ...1993 Volume 41 Issue 3 Pages 516-521
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS9-(cis-3-Hydroxymethyl-2-methylenecyclobutyl)guanine (3b) and 9-(3-methylene-trans-2-hydroxymethylcyclobuty)guanine (4b) were prepared from N2-isobutyryl-9-[trans-trans-2, 3-bis(hydoxymethy)cyclobutyl]guanine (2f) or 2, 3-bis(hydroxymethy)-1-cyclobutanol (7b)- Carbocyclic oxetanocin analogues (A, 1d; G, 2d) and related compounds inclusing 4b were assayed against a broad variety of viruses. It apperred that the activity of 2d against herpes simplex virus(HSV) and varicella-zoster virus (VZV) at least partially depends on phosphorylation by the virus-induced thymidine kinase (TK). Although 1d and 2d are inhibitory to the replication of human immunodeficiency virus (HIV), they are quite toxic to proliferating human T-lymphocytes.View full abstractDownload PDF (951K) -
Hiroki UEDA, Yuji MOMOI, Tetsuyuki IKEDA, Hisao KAKEGAWA, Hideki MIYAT ...1993 Volume 41 Issue 3 Pages 522-524
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel series of trans-guanidinomethylcyclohexanecarboxylic acid (trans-GMCHA) arylamides was synthesized.The several trans-GMCHA arylamide derivatives showed more potent inhibitory effects on the stress- and HCl-ethanol-induced gastric ulcers than cetraxate in rats. In acute toxicity studies in mice, most amides showed such severe toxicity that all mice injected with these compounds (50 mg/kg, i.p.) died. However, mice injected with the trans-GMCHA (2', 3'- and 4'-ethoxycarboxy)phenylamide (7, 8 and 9) which bear an alkyloxycarbonyl group at benzene ring survived.From these results, trans-GMCHA (2'-ethoxycarbonyl)phenylamide (7) was selected as a promising anti-ulcer agent.View full abstractDownload PDF (529K) -
Koichi KAWASAKI, Toshiki TSUJI, Katuhiko HIRASE, Masanori MIYANO, Sach ...1993 Volume 41 Issue 3 Pages 525-528
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious peptides related to N-terminal portion of fibrin α-chain were synthesized by the solution method and the solid-phase method, and their inhibitory effect on fibrinogen/thrombin clotting was examined. Extension of peptide chain from N-terminal tripeptid decreased the inhibitory effect. The most potent effect was shown by N-terminal decapeptide analog, H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2.View full abstractDownload PDF (833K) -
Yuji ISHIHARA, Masaomi MIYAMOTO, Takahiro NAKAYAMA, Giichi GOTO1993 Volume 41 Issue 3 Pages 529-538
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInhibitors of acetylcholinesterase (AChE) have been designed based on a working hypothesis of the enzyme's active site. These compounds were tested for their inhibitory activities on AChE and ω-[N-ethyl-N-(phenylmethyl)amino]-1-phenyl-1-alkanones (3) were found to be potent inhibitors. Various analogues of 3 were prepared to study the effect on AChE inhibition of partial restriction of conformation. Compounds with potent AChE inhibition were further evaluated in terms of central selectivity : the ratio of central action (ameliorationg effect on scopolamine-induced memory impairment using a T-maze alternation task) to peripheral action.View full abstractDownload PDF (1376K) -
Setsuo SAITO, Yuka SASAKI, Kaoru KURODA, Yasunobu HAYASHI, Shigeya SUM ...1993 Volume 41 Issue 3 Pages 539-543
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStepwise glycosidation was adopted for the construction of glycyrrhetic acid β-glycosides (27-30) having β(1→2)-linked disaccharides such as 2-O-β-D-flucuronopyranosyl-β-D-glucopyranose, 2-O-β-D-glucuronopyranosyl-β-D-galactopyranose, 2-O-β-D-glucopyranosyl-β-D-glucuronopyranose and 2-O-β-D-galactopyranosyl-β-D-glucuronopyranose. In the first glycosidation, 2-O-trichloroacety-β-D-pyranosyl chlorides (9-11) were utilized as starting sugar derivatives to react with methyl glycyrrhetinate (5) : Glycosidation of 5 with 9 and 10 gave β- and α-monoglycosides (12) and (13), and (15) and (16), respectively. Treatment of the β-glycoside 12 and 15 with ammonia-saturated ether gave products (14) and (17), respectively. The glycosidation of 5 with 11 followed by treatment with ammonia-saturated ether gave compounds (18) and (19), respectively. The second step glycosidations of 14 and 17 with methyl 2, 3, 4-tri-ο-acetyl-α-D-glucuronatopyranosyl bromide (20) gave diglycoside derivatives (23) and (24), respectively, and that of 18 with 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide (21) and -α-D-galactopyranosyl bromide (22) gave deglycoside derivatives (25) and (26), respectively. The removal of the protecting groups of 23-26 gave diglycosides 27-30, respectively, having a β-D-glucuronopyranose (β-D-glcUA) as one of two sugar components in the molecules. The cytoprotective effects of the synthesized glycosides 27-30 on carbon tetrachloride (CCl4)-induced hepatotoxicity in vivo were compared with deglycosides 31-33 having only neutral sugar components, and naturally occurring glycyrrhizin (34) having two acidic sugar components (β-D-glcUA). While glycosides 31-33 had no cytoprotective effect, glycosides 27-30 showed potent effects. Especially, 27 and 28, having a β-D-glcUA as the terminal sugar component, were more effective meterials against hepatic injury than glycyrrhizin 34.View full abstractDownload PDF (785K) -
Jingyi HE, Akimasa SHIBUKAWA, Terumichi NAKAGAWA, Hiroo WADA, Hiroya F ...1993 Volume 41 Issue 3 Pages 544-548
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel HPLC system was developed with an achiral/chiral coupled column for the direct injection analysis of atenolol (AT) enantiomers in plasma. The system consists of a size-exclusion column, an ODS silica column and a newly developed β-cyclodextrin perhenylcarbamate(ph-β-CD)-bonses silica column connected in a series via two switching valves. The neat plasma sample was directly injected onto the size-exclusion column, and the deproteinzed fraction of AT enantiomers was concentrated on the ODS silica column. The enantimers were then transrerred and separated mutually on the ph-β-CD silica column. The calibration line for each of the AT enantiomers was linear in the range of plasma concentration of 10-200 ng/ml (r>0.9997) with good reproducibility (CV<9.7%, n=20). The recoveries from plasma were almost complete (>97.4%) for both enatiomers. One analysis finished within 30 min. The developed system was applied to the enantioselective determination of plasma concentration-time curve of AT after the oral administration of racemic AT to a healthy volunteer.View full abstractDownload PDF (747K) -
Tetsuya SAITA, Mitsuo KATANO, Hisashi MATSUNAGA, Hiroshi YAMAMOTO, Hir ...1993 Volume 41 Issue 3 Pages 549-552
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntitumor polyacetylenic alcohol, panaxynol, was isolated and purified from a powder of the root of Panax ginseng C. A. MEYER. Panaxynol inhinited the growth of various kinds of cultured tumor cell lines in a dose-dependent manner.In this paper we demonstrated the first specific antibody prosuction against panaxynol. Anti-panaxynol antibody was elicited in rabbits by immunization with panaxynol hemisuccinate-bovine serum albumin conjugate (panaxynol hemisuccinate-BSA conjugate). An enzyme immunoassay (EIA) for the determination of panaxynol was established using a double-antibody technique. The EIA was highly specific against panaxynol although the antibody showed a minimal cross-reactivity with other types of polyacetylenic alcohol, i.e. panaxydol (12.0%) and panaxytriol (0.77%).Panaxynol at a concentration as low as 6.4 ng/ml can be detected. Using this assay we reconfirmed the rapid consumption of panaxynol by target tumor cells in an in vitro-culture system. The anti-panaxynol antibody may be a valuable tool for studies of the biological properites of polyacetylenic compounds.View full abstractDownload PDF (645K) -
Baoliang CUI, Junei KINJO, Toshihiro NOHARA1993 Volume 41 Issue 3 Pages 553-556
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the bark of Robinia pseudo-acadia L., six new triterpene glycosides, Rpbiniosides E-J, were isolated and their structures were elucidated as abrisapogenol B 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosy(1→2)-β-D-glucuronopyranoside (1), abrisapogenol B 3-O-α-L-rhamnopyranosy(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranoside (2), 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl abrisapogenol B 22-O-α-L-rhamnopyranoside (3), 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranosyl abrisapogenol B-22-O-α-L-rhamnopyranoside (4), 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl abrisapogenol E 30-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (5) and 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyanosyl abrisapogenol E 30-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (6), respectively.View full abstractDownload PDF (759K) -
Yi DING, Rui-Hua TIAN, Chong-Ren YANG, Yan-Yong CHEN, Toshihiro NOHARA1993 Volume 41 Issue 3 Pages 557-560
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a previous paper, we peported the isolation and structure determination of three new steroidal saponins, dongnosides C (3), D (2) and E (1) from the dried fermented residues of leaf-juices of Agave sisalana forma Dong No. 1. In a continuing study on this plant, two additional new major steroidal saponins, named dongnosides B (4) and A (5), were obatained. Their structures were characterized respectively as tigogenin 3-O-α-L-rhamonpyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside and 3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside on the basis of chemical and physicochemical evidence.View full abstractDownload PDF (736K) -
Yoshiyasu FUKUYAMA, Yuuko KIRIYAMA, Junko OKINO, Mitsuaki KODAMA, Hide ...1993 Volume 41 Issue 3 Pages 561-565
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew alkenyl-1, 4-benzoquinones, ardisianones A (1) and B (2), and the known maesanin (3) an 5-lipoxygenase inhibitors have been isolated from the rhizome of Ardisia japonica. Their structures have been elucidated as 2-methoxy-6-[(Z)-10'-pentadecenyl]-1, 4-benzoquinone and 5-hydroxy-2-methoxy-6-[(Z)-8'-tridecenyl]-1, 4-benzoquinone, respectively, on the basis of spectroscopic data and chemical degradation. Ardisianone A (1), maesanin (3) and belamcandol A (7) have been synthesized starting from belamcandol B (6), readily prepared by Wittig reaction between 9-(2-tetrahydropyanylox)nonanal and 3, 5-dimethoxybenzyltriphenylphsophonium bromide followed by selective demethylation with sodium thioethoxide.View full abstractDownload PDF (886K) -
Takayuki ASANO, Tetsuya MURAYAMA, Yasuaki HIRAI, Junzo SHOJI1993 Volume 41 Issue 3 Pages 566-570
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo monoterpene glycosides, tentatively named OJV-I (1) and OJV-II (2), and eight steroidal glycosides, tentatively named OJV-III (3), OJV-IV (4), OJV-V (5), OJV-VI (6), OJV-VII (7), OJV-VIII (8), OJV-IX (9) and OJV-X (10), were isolated from the butanol-soluble fraction of the fresh subterranean part of Ophiopogon japonicus KER-GAWLER cv. Nanus. Among these compounds, 1, 2, 3, 4, 5, 6 and 7 were identified as l-bornelo O-β-D-glucopyranoside, l-borneol O-β-D-apiofuranosyl (1→6)-β-D-glucopyranoside, ophiopogonin B, glycoside C, ophiopogonin D, Ls-10, and ruscogenin 1-O-sulfate, respectively. The structures of compounds 8, 9, and 10 were established to be (23S, 24S, 25S)-23, 24-dihydroxyruscogenin l-O-[α-L-rhamnopyranosyl(1→2)] [β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside 24-O-β-D-fucopyranoside, (23S, 24S, 25S)-23, 24-dihyrdroxyruscogenin 1-O-[α-L-2, 3, 4-tri-O-acetylrhamnopyranosyl(1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside 24-O-β-D-fucopyranoside, and (23S, 24S, 25S)-23, 24-dihydroxyruscogenin 1-O-[α-L-4-O-acetylrhamnopyranosyl(1→2)] [β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside 24-O-β-D-fucopyranoside, respectively.View full abstractDownload PDF (978K) -
Munehisa ARISAWA, Hua BAI, Miwa SHIOJIMA, Toshimitsu HAYASHI, Yasuhiro ...1993 Volume 41 Issue 3 Pages 571-574
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree novel flavonoids, chrysograyanone (1), chrysoquinone A (2), and chrysosplenoside H (3), have been isolated from fresh plants of Chrysosplenium grayanum MAXIM. (Saxifragaceae) and their structures were determined to be 5-hydroxy-2-(1, trans-5-dihydroxy-4-methoxy-5-methoxycarbonyl-2-oxo-cyclopent-3-enyl)-3, 7-dimethoxyhromone (1), 2', 5'-dihydro-5-hydroxy-3, 7, 4', 6'-tetramethoxyflavone-2', 5'-dione (2), and 5, 2'-dihydroxy-3, 6, 7, 4', 5'-pentamethoxyflavone (brickellin)-2'-O-β-D-glucopyranoside (3) on the basis of spectroscopic evidence and X-ray analysis.View full abstractDownload PDF (717K) -
Katsumi MATSYZAKI, Toshi IMAOKA, Mina ASANO, Koichiro MIYAJIMA1993 Volume 41 Issue 3 Pages 575-579
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral model membrane systems have been reported to predict the skin permaebility of drugs, but model membranes using stratum corneum (SC) lipids have never been reported. Thus, we developed a model membrane system for drug permeation study by fixing liposomes composed of SC lipids (ceramides, palmitic acid, cholesterol, and cholesterol-3-sulfate) onto a supporting filter, Biodyne B. The permeability of several drugs with different lipophikicities was investigated. Permeability increased with drug lipophilicity, estimated from the octanol/buffer solubility ratio of the drug. For relatively polar drugs, however, the permeability was almost constant, and very close to the value of a K+ ion, suggestiong the membrane has both lipidic and aqueous pathways. Drug permeability through our system was compared with that through guinea pig skin. A good corelation (r=0.880) was observed, although the former was one order of magnitude greater than the latter. Our model system will be useful not only for parctical application, but also for basic studies, such as the elucidation of the relationships between SC lipid composition and drug permeability.View full abstractDownload PDF (1066K) -
Satoru WATANO, Tsutomu HARADA, Keijiro TERASHITA, Kei MIYANAMI1993 Volume 41 Issue 3 Pages 580-585
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new practical method of controlling the moisture content of particles in an aqueous polymeric coating by a tumbling fluidized bed is described. The method was based on the on-line measurement and feedback control of moisture content by use of an IR (infrared) moisture sensor. Spherical core particles made of crystalline cellulose were coated in the tumbling fluidized bed by atomizing the suspension of enteric acrylic copolymer (Eudragit L30D-55). The influence of moisture control, conducted with different methods (PID (proportional-integral-derivative) control and on-off control), on the drug release rate and on the agglomeration tendency of coated particles was investigated. It was found that moisture control by the PID control method was useful for producing the desired coated particles which exhibited excellent properties in delayed release with a low agglomeration tendency.View full abstractDownload PDF (927K) -
Ryuzo ISHINO, Hisakazu SUNADA1993 Volume 41 Issue 3 Pages 586-589
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to examine the function of a wax matrix system as a barrier for the controlled release of oral dosage forms, reservoir devices were prepared and dissolution tests were conducted. The permeability coefficients of isoniazid through wax matrix layers consisting of various proportions of α-lactose monohydrate and hydrogenated castor oil were determined coincidently with the penetration rate constants of water into the wax matrix layers. To elucidate the barrier function relating to control of the drug release rate, dry-coated tablets in which the outer shell was formed with the wax matrix system were prepared. The dissolution behavior of isoniazid from the dry-coated tablets coincided with the simulation result calculated using the obtained permeability coefficient and penetration rate constant.View full abstractDownload PDF (724K) -
Akihiko ITO, Yuka DOBASHI, Masayasu SUGIHARA1993 Volume 41 Issue 3 Pages 590-594
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dividing properties of scored tablets were examined, considering the relationship with the dynamic characteristics of various mixed puwders.Powdered mixtures of lactose and cornstarch (SL/CS), lactose and microsrystalline cellulose (SL/MCC), and lactose and Perfiller[○!R] (SL/Perfiller[○!R]) in various ratios were used. The cohesive force (C), angle of internal friction(δ), flow factor (FF) and constant (a) in Kawakita's equation for tapping compaction were measured as dynamic characteristics of each powdered mixture.A significant correlation was obtained between the coefficient of varlation of the divided tablet weight and the C value for SL/CS and SL/Perfiller[○!R] mixtures and the δ value for SL/MCC mixtures. The coefficient of variation of divided tablet weight decreased with decrease in the C value for SL/CS and SL/Prefiller[○!R] mixtures and with increase in the δ value for SL/MCC mixtures. Significant correlation was also obtained between the logarithms of the dividing strength of the scored tablets and tha a value for SL/CS mixtures, the FF value for SL/Perfiller[○!R] mixtures and the δ value for SL/MCC mixtures. Tablet dividing strength increased with decrease in the a value for SL/CS mixtures, with increase in the FF value for SL/Perfiller[○!R] mixtures and with increase in the δ value for SL/MCC mixtures. The dynamic characteristics of a powdered mixture influencing the tablet dividing properties thus were suggested differ due to the physical properties of the additives, but tablet dividing properties were ultimately dependent on the formation of a uniform and denser packing of the powdered mixtures.View full abstractDownload PDF (696K) -
Eihei FUKUOKA, Midori MAKITA, Shigeo YAMAMURA1993 Volume 41 Issue 3 Pages 595-598
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVariation of the degree of crystallinity, lattice-disorder and crystallite size of pharmaceuticals with compression were investigated by X-ray powder diffraction method. The degree of crystallinity and lattice-disorder parameter were determined by Ruland's method. Crystallite size was calsulated by Scherrer's equation after correction for the instrumental broadening of the diffragtion line. Crystalline powders of aspirin and nicotinic acid were used as samples.The degree of crystallinity, lattice-disorder and crystallite size of pharmaceuticals varied with compression. In aspirin, the degree of crystallinity and crystallite size calculated from the profile of 100 reflection decreased and lattice-disorder increased with compression. The degree of crystallinity and crystallite size remarkably decreased immediately after compression and then recovered gradually with stress relaxation. In nicotinic acid powder, however, although the degree of crystallinity decreased and lattice-disorder increased with compression, these features did not recover with stress relaxation.View full abstractDownload PDF (615K) -
Yasuki KATO, Kyoko WATANABE, Masashi NAKAMURA, Toshihito HOSOKAWA, Eij ...1993 Volume 41 Issue 3 Pages 599-604
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe in vivo elimination and tissue distribution (2 h after administration) of various types of formulations of α-tocopherol as a model drug were examined in rats. An organic cosolvents formulation of α-tocopherol (α-tocopherol/EtOH/polyethylene glycol 400) was rapidly removed from the blood circulation, the ratio of the distributed α-tocopherol was 20% in the lungs, about 70% in the liver and about 10% in the spleen. The main reason for this was considered to be the appearance of droplets more than 10 μm in diameter in the blood. Elimination of the micelle formulation using Brij58 from the blood was the most rapid, followed by Tween80 and HCO60. This order is thought to be due to the difference in the polyoxyethylene group among these surfactants.In liposome formulations, liposomes having a diameter of about 80 nm were the most stable in the blood circulation, and α-tocopherol was distributed in the reticuloendothelial system (RES) in the smallest ratio. The uptake of liposomes by the spleen and lungs depended on the liposome size. The uptaka by the liver was in the decreasing order of 28 nm » 42nm, 151 nm, 195 nm, 3656 nm > 106 nm > 75 nm.The 100 nm lipid emulsion was eliminated form the blood more rapidly than the 100 nm liposome formulation.View full abstractDownload PDF (906K) -
Nobuo OKABE, Misa HOKAZE1993 Volume 41 Issue 3 Pages 605-607
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structure of the copper(II) chloride complex of the thyroid hormone precursor, 3, 5-diiodo-L-tyrosine, (C9H9I2NO3·CuCl) was determined by the X-ray diffraction method. The space group is P212121, with cell dimensions a=8.405(2), b=20.694(3) and c=7.532(3) Å. The structure was refined to R=0.064 for 1374 reflections(I >3σ(I)). The Cu(II) ion is six-coordinated by interaction with one amino nitrogen, two carboxyl oxygens and one chlorine atom in a square plane, and the phenol iodine and oxygen atoms in axial positions. Three-dimensional arrangement of the molecules are stabilized by two hydrogen bonds of O-H(pheno)··O(carboxyl), and N-H(amino)··O(carboxyl).View full abstractDownload PDF (480K) -
Izumi MATSUURA, Taisei UEDA, Nobutoshi MURAKAMI, Shin-ichi NAGAI, Jins ...1993 Volume 41 Issue 3 Pages 608-610
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 5-aminopyrimidln-4(3H)-one (1) with Lewis acidic metal salts such as zinc chloride, zinc bromide, zinc iodide, aluminum chloride, aluminum bromide, nickel chloride, copper(I) chloride, or copper(I) iodide in the presence of oxidizing agents such as ceric ammonium nitrate, ammonium persulfate, or phenyliodine(III) diacetate in methanol gave 2-methoxy-1H-imidazole (2).View full abstractDownload PDF (421K) -
Takashi ADACHI, Mika SAITO, Joji SASAKI, Yasuko KARASAWA, Hiroaki ARAK ...1993 Volume 41 Issue 3 Pages 611-613
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(6R)-6-Hydroxy-, (6S)-6-hydroxy- and (18S)-18-hydroxyeburnamonines were obtained by microbial conversion of (-)-eburnamonine using Mucor circinelloides and Streptomyces violens. Their structures were determined by analyses of the mass, 1H- and 13C-NMR spectra. (-)-Eburnamonine and the three hydroxylated compounds showed cerebral protecting effects against potassium cyanide intoxication in mice.View full abstractDownload PDF (495K) -
Ermitas ALCALDE, Lluisa PEREZ-GARCIA, Jordi FRIGOLA1993 Volume 41 Issue 3 Pages 614-616
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Alkylation of (E)-2-[2-(4-pyridyl)vinyl]-1H-benzimidazole (10), obtained by two different approaches, affords the title salts 4-6, deprotonation of which results in the new (E)-1-alkyl-4-[2-(benzimidazolyl-2-idene)ethylidene]-1, 4-dihydropyridines (7 and 8) with a betaine character. Their biological properties have also been examined.View full abstractDownload PDF (567K) -
Akira INADA, Midori SOMEKAWA, Hiroko MURATA, Tsutomu NAKANISHI, Haruku ...1993 Volume 41 Issue 3 Pages 617-619
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA 24-epimeric mixture of a new triterpenoid, 24-hydroxydammara-20, 25-dien-3-one (1), and two known triterpenoids, moronic acid (2) and betulonic acid (3), were isolated from leaves of Chisosheton macrophyllus KING, and the inhibitory effects of these triterpenoids on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate were tested.View full abstractDownload PDF (522K) -
Makoto MIZOGUCHI, Masanobu SHIGA, Kazumi SASAMOTO1993 Volume 41 Issue 3 Pages 620-623
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew chromogenic hydrogen donors (1a-c) for peroxidase-catalyzed oxidation were synthesized and demonstrated to be potentially useful for spectrometric determination of hydrogen peroxide. Under oxidative conditions these compounds exhibit, without an additional component, intense blue colors at ca. 650 nm with higher sensitivities toward hydrogen peroxide than those of conventional reagents. The detection limit of hydrogen peroxide using these compounds was 0.1 μM under serum-free conditions.View full abstractDownload PDF (614K) -
Toshihiro AKIHISA, Wilhelmus C.M.C.KOKKE, Yoshihiro HAYASHI, Yumiko KI ...1993 Volume 41 Issue 3 Pages 624-626
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIsolation and identification of five triterpene alcohols, twelve 4α-methylsterols, and seventeen sterols as acetyl derivatives from the unsaponifiable lipid of the methanol extract of Gleichenia japonica were described. This is the first report on the identification of (22E, 24R)-4α, 23-dimethyl-5α-ergosta-7, 22-dien-3β-ol (7-dehydrodinosterol) and(22E, 24R)-4α-methyl-5α-ergosta-7, 22-dien-3β-ol in a terrestrial plant.View full abstractDownload PDF (492K) -
Muneaki KURIMURA, Kazuo ACHIWA1993 Volume 41 Issue 3 Pages 627-629
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor outstanding the structere-activity relationship of lipopeptide derivatives, high biologically active lipopeptide derivatives with an achiral lipo-part were newly synthesizedView full abstractDownload PDF (377K) -
Masayuki YOSHIKAWA, Emiko HARADA, Atsuhiro KAWAGUCHI, Johji YAMAHARA, ...1993 Volume 41 Issue 3 Pages 630-632
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new labile monoterpenes named paeonisuffrone and paeonisuffral were isolated from Chinese Moutan Cortex, the dried root of Paeonia suffruticosa ANDREWS. The absolute stereostructures of peaonisuffrone and paeonisuffral were elucidated on the basis of chemical and physicochemical evidence which included the application of a modified Mosher's method and lipase catalyzed debenzoylation.View full abstractDownload PDF (504K) -
Tomonori HOSHIKO, Hiroki ISHIHARA, Mitsumasa SHINO, Nobuyuki MORI1993 Volume 41 Issue 3 Pages 633-635
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of trans-3, 4-bis-(3, 4-dihydroxyphenyl)pyrrolidine by the Michael reaction of esterenolate with nitro olefin is described. This compound was expected to be the agonist toward dopamine (DA1) receptor with equipotent affinity and to be more selective than dopamine itself.View full abstractDownload PDF (446K) -
Masayuki YOSHIKAWA, Nobutoshi MURAKAMI, Yasunao INOUE, Shoko HATAKEYAM ...1993 Volume 41 Issue 3 Pages 636-638
Published: March 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn optically active pseudo-sugar, pseudo-α-D-arabinofuranose, was synthesized from D-arabinose in favorable overall yield by using a stereoselective formation of branched nitropyranose as the key step.Furthermore, two biologically active pseudo-β-D-arabinofuranosylnuleosides, (+)-cyclaradine and (+)-1-pseudo-β-D-arabinofuranosyluracil, were synthesized via Michael-type reactions of nucleic acid bases and a nitrocyclopentene derivative which was prepared from a synthetic intermediate of pseudo-D-arabinofuranose.View full abstractDownload PDF (497K)
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