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Volume 38, Issue 7
Displaying 1-50 of 62 articles from this issue
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Toshimasa ISHIDA, Yasuko IN, Masatoshi INOUE, Takushi KURIHARA, Kazuhi ...1990 Volume 38 Issue 7 Pages 1803-1809
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo experimentally clarify a possible stereostructure-activity relationship proposed for H2-receptor antagonists, three 5-aminophenylimidazoles (1, 2 and 3), in which respective amino groups are located on the ortho, meta and para positions of the benzene ring, were synthesized and examined for their conformational characteristics using X-ray diffraction and proton nuclear magnetic resonance ( 1H-NMR) methods, and for antiulcer activities on rats and H2-receptor antagonist activities in guinea pig. The ortho isomer 1, which preferentially formed an intramolecular N-H (amino)…N (imidazole) hydrogen bond, showed the highest antiulcer activity with half the efficacy of cimetidine. On the other hand, none of 1, 2 and 3 showed significant H2-receptor antagonist activity. Based on these results, the conformational characteristic for the exhibition of antiulcer activity has been discussed.View full abstractDownload PDF (969K) -
Saburo SHIMABAYASHI, Yoshio TANIZAWA1990 Volume 38 Issue 7 Pages 1810-1814
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTransformation of amorphous calcium phosphate (ACP) to hydroxyapatite (HAP) and subsequent crystal growth of HAP were retarded in the presence of phosphorylated polyvinylalcohol (Phos.PVA) and phosphoserine (PSer), while the mother compounds, polyvinylalcohol (PVA) and serine (Ser), showed no specific effect on these factors over the concentration range investigated. The retardation was caused through the competitive adsorption between inorganic phosphate ion (Pi, one of the lattice ions) and the phosphate group of the organic compounds (i.e., Phos. PVA and PSer) for the active growth sites on the HAP crystal or nucleus. Phos. PVA was about 20 times stronger than PSer in its effect owing to the fact than the thick adsorption layer of the former repels Pi more efficiently than the thin adsorption layer of the latter. These results suggest that high molecular phosphorylated compounds such as phosphoproteins are more significant in regulation/retardation of biological mineralization/crystallization in mammalian body than low molecular phosphorylated compounds such as PSer.View full abstractDownload PDF (905K) -
Mitsunobu DOI, Toshimasa ISHIDA, Masatoshi INOUE1990 Volume 38 Issue 7 Pages 1815-1818
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(5S, 7S, 8S)-(-)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide (U69, 593) is a potent agonist to opioid κ-receptor. The crystal structure of U69, 593 has been analyzed by the X-ray diffraction method. The molecule, as a whole, took an open conformation, and four cyclic rings composing the main skeleton were far apart from each other. The N and O atoms substituted for the cyclohexane ring were all in the equatorial position. The best planes of two 5-membered rings were almost perpendicular to that of the cyclohexane ring, and the N-methylamide linkage was also orthogonal to this ring plane. The conformation of the U69, 593 molecule was compared with other κ-agonists.View full abstractDownload PDF (604K) -
Shoko YOKOYAMA, Fumio UEDA, Tadao FUJIE1990 Volume 38 Issue 7 Pages 1819-1823
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rates of release of thiamine disulfide (TDS) from odd-numbered fatty acids-TDS complexes, (C2n-1)6(TDS), were determined at various temperatures, and the thermodynamic quantities in the kinetics for the release of TDS from the complexes were estimated.The rate of release of TDS from the complexes decreased with increasing carbon number in the odd-numbered fatty acid and increased at a higher temperature. The values of activation Gibbs energy ΔG〓 and activation enthalpy ΔH〓 for the release of TDS from the complexes were positive. The value of activation entropy ΔS〓 was negative.The results obtained for(C2n-1)6 (TDS) were compared with the previous results obtained for the even-numbered fatty acids-TDS complexes, (C2n)6(TDS). The plots of the release rate constant of TDS from the complexed against the carbon numbers of the constituent fatty acids showed a zig-zag pattern which indicates a downward convex at an odd-numbered position. Furthermore, the plots of the positive values of ΔH〓 against the carbon numbers of the constituent fatty acids showed a zig-zag line which indicates an upward convex at an odd-numbered position, while the plots of the negative values of ΔS〓 showed a zig-zag line which indicates a downward convex at an odd-numbered position. The release of TDS from (C<2n-1>)6(TDS) is more disadvantageous from the activation enthalpic viewpoint and more advantageous from the activation entropic viewpoint than (C2n)6(TDS). It is found that the release of TDS from (C2n-1)6(TDS) is an enthalpically controlled reaction, making the release more disadvantageous due to the enthalpic effect. The zig-zag line for the release rate of TDS from the complexes can be explained by the thermodynamic parameters of the transition intermediate.View full abstractDownload PDF (733K) -
Machiko ONO, Ichiro ARAYA, Reiko TODOROKI, Shinzo TAMURA1990 Volume 38 Issue 7 Pages 1824-1831
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydrolysis and alcoholysis of carboxamides derived from primary aliphatic amines were achieved under mild conditions. Amide exchange reaction between carboxamides and N1-acyl-N1, N2-di (p-nitrophenyl) formamidines (1) gave N1-acyl-N1-alkyl-N2-(p-nitrophenyl)formamidines (2) which were readily hydrolyzed or alcoholyzed to give N1-alkyl-N2-(p-nitrophenyl)formamidines (4) and carboxylic acid or its ester. Compounds 4 were hydrolyzed to give aliphatic amine and N-formyl-p-nitroaniline in the presence of acetic acid or hydrochloric acid at room temperature. For the alcoholysis of N-acyl derivatives of amino alcohols, protection of the hydroxyl substituent by an acyl group was essential because the reaction of 1 and N-acyl derivatives of amino alcohols was quite complex. Alcoholysis of N-ethyl-N, N'-ethylenebis (p-chlorobenzamide) (8a) by this method gave N-(2-aminoethyl)-N-ethyl-p-chlorobenzamide (8b). Thus, the selective alcoholysis of diacyl derivative of diamines, which contain primary and secondary amino groups, was achieved.View full abstractDownload PDF (1303K) -
Jun-etsu IGARASHI, Yoshinari KAWAKAMI, Toshio KINOSHITA, Sunao FURUKAW ...1990 Volume 38 Issue 7 Pages 1832-1835
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the reaction of silylated butadiene derivatives (1) with dimethyl acetylenedicarboxylate (DMAD), it is proposed that the reactivities of the dienes can be predicted from the carbon-13 nuclear magnetic resonance chemical shifts of the terminal methylene carbons (δ13C-4) of the dienes based on the following linear relationships, a) total electron densities against δ13C-4; b) ln k against 1/[ELUMO(DMAD)-EHOMO(diene)]; c) ln k against δ13C-4. The total electron densities and energy levels of highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the dienes were calculated by the modified neglect of diatomic overlap (MNDO) method.View full abstractDownload PDF (653K) -
Synthetic Anthracyclines : Regiospecific Total Synthesis so D-Ring Thiophene Analogues of DaunomycinYasuyuki KITA, Masayuki KIRIHARA, Jun-ichi SEKIHACHI, Ryuichi OKUNAKA, ...1990 Volume 38 Issue 7 Pages 1836-1843
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe key anhydride 2-acetoxy-[2-carboxy-5-(trimethylsilyl)thiophen-3-yl]acetic acid anhydride (8), prepared from (2-carboxythiophen-3-yl)acetic acid (5), underwent a strong base-induced cycloaddition reaction with the chloroquinone acetal (11) to give the 7, 7-ethylenedioxy-2-trimethylsilyl-6, 7, 8, 9-tetrahydroanthra[2, 3-b]thiophene-5, 10-dione (12) regioselectively. Similarly, the regioisomeric 8, 8-ethylenedioxy-2-trimethylsilyl-6, 7, 8, 9-tetrahydroanthra[2, 3-b]thiophene-5, 10-dione (30) was obtained by the strong base-induced cycloaddition reaction of 8 with the chloroquinone acetal (29). These cycloadducts (12 and 30) were converted to D-ring thiophene analogues (28 and 38) of daunomycin (1a). Another D-ring thiophene analogue (42) which has a trimethylsilyl substitutent in the D-ring was also prepared.View full abstractDownload PDF (1362K) -
Jer-Huei LIN, Makoto ISHIMATSU, Takashi TANAKA, Gen-ichiro NONAKA, Its ...1990 Volume 38 Issue 7 Pages 1844-1851
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTogether with eleven known compounds (1-11), seven new tannins, 3-desgalloylterchebin (12), macaranins A, B and C, and macarinins A, B and C, have been isolated from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG. (Euphorbiaceae). Macaranins A (14), B (13) and C (17) have been determined on the basis of chemical and spectroscopic evidence to be hydrolyzable tannins possessing a novel acyl group (macaranoly group) at the 3, 6-positions of the 1C4 (or skew boat) β-D-glucopyranose ring, while macarinins A (18), B (15) and (16) were characterized as those having a tergalloyl group at the same positions.View full abstractDownload PDF (1161K) -
Hiroshi IRIE, Ritsuko MATSUMOTO, Masataka NISHIMURA, Yong ZHANG1990 Volume 38 Issue 7 Pages 1852-1856
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA synthesis of (±)-heritol, a sesquiterpene lactone, was accomplished starting from methyl 3-methoxy-4-methylbenzoate using an intarmolecular Witting reaction as a key reaction for constructing the butenolide ring.View full abstractDownload PDF (914K) -
Richard C. CAMBIE, Allick R. LAL, Clifton E. F. RICKARD, Nobutoshi TAN ...1990 Volume 38 Issue 7 Pages 1857-1861
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new compounds were isolated from the heartwood of the Fijian tree Fagraea gracilipes A. Gray in addition to methyl p-coumarate, methyl caffeate, methyl sinapate, and the secoiridoid glucoside sweroside. The new compounds have been identified as methyl syringate α-L-rhamnoside, (Z)-5-ethylidene-3, 4, 5, 6-tetrahydro-cis-6, 8-dimethoxy-1H, 8H-pyrano[3, 4-c]pyran-1-one, (Z)-5-ethylidene-3, 4, 5, 6-tetrahydro-trans-6, 8-dimethoxy-1H, 8H-pyrano[3, 4-c]pyran-1-one, 3-O-sinapoyl D-glucose and 3'-O-sinapoyl sweroside by spectroscopic methods, chemical conversion and X-ray analysis.View full abstractDownload PDF (833K) -
Fumiyuki KIUCHI, Xing CHEN, Yoshisuke TSUDA1990 Volume 38 Issue 7 Pages 1862-1871
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylation of dibenzoylmethanes with diazomethane always gave Z-β-methoxychalcones, which are the products of kinetically controlled methylation of chelated enol forms of β-hydroxychalcones. Z-β-Methoxychalcones were thermodynamically unstable and readily isomerized into more stable E-isomers on contact with silica gel, on keeping in polar solvents, or on exposure to light. The structures of both isomers of the simplest β-methoxychalcone were determined by X-ray crystal structure analysis. All β-methoxychalcones prepared were fully characterized by spectroscopic methods, revealing that the E- and Z-isomers are distinguishable in terms of ultraviolet and 13C-nuclear magnetic resonance spectra, and nuclear Overhauser effect between the β-methoxyl group and H-8 proton. The spectral data reported for natural β-methoxychalcones, methylpongamol and praecansone A, are attributable to the E-isomers.View full abstractDownload PDF (1354K) -
Hiromichi FUJIOKA, Hirofumi YAMAMOTO, Hirokazu ANNOURA, Makoto MIYAZAK ...1990 Volume 38 Issue 7 Pages 1872-1876
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA New chiral AB-building block (5) for preparing optically active anthracyclinones was synthesized via compound 13a, which was obtained by the stereoselective nucleophilic addition of (trimethylsilyl)ethynylmagnesium chloride to the chiral 6-bromo-1-oxo-β-tetralone 1-acetal (12) derived from (-)-(2S, 3S)-1, 4-dimethoxy-2, 3-butanediol. Synthesis of (-)-7-deoxydaunomycinone [(-)-4] was achieved through a regiospecific condensation of 5 and 4-acetoxy-8-methoxyhomophthalic anhydride (18). The optical purity (100% ee) of (-)-4 was unambiguously confirmed by high performance liquid chromatographic analysis of (±)-4 and (-)-4 on a chiral column and also by proton nuclear magnetic resonance examination of the methylated compounds, (±)- and (-)-21, using the chiral shift reagent, tris[3-(trifruoromethylhydroxymethylene)-d-camphorato]europium(III) [Eu(tfc)3].View full abstractDownload PDF (935K) -
Yoshio TAKEDA, Tetsuro FUJITA, Han-dong SUN, Yoshinori MINAMI, Masamit ...1990 Volume 38 Issue 7 Pages 1877-1880
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of isodonal and rabdolasional were re-examined by means of two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and were revised to 1 and 2 from the previously reported structures, 3 and 4. The structures of the chemically correlated diterpenoids, isodonoic acid and trichodonin were also revised to 7 and 8, respectively.View full abstractDownload PDF (511K) -
Chihiro ITO, Shiho TANAHASHI, Kazuko FUJIWARA, Mayumi NAKAGAWA, Motoha ...1990 Volume 38 Issue 7 Pages 1881-1885
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first isolation of the unique homoacridone alkaloids, citropone-A (1), -B (2), and -C (3) from the root or stem bark of some cultivated Citrus plants is described. The structure of citropone-A (1) was established unequivocally by spectrometric and single-crystal X-ray analyses, while citropone-B, which has the same skeleton as 1, was assigned structure 2 by comparison of the 1H- and 13C-nuclear magnetic resonance spectra with those of 1. The structure of citropone-C was proposed as formula 3 on the basis of spectrometric analyses using H-C long-range two-dimensional correlation spectroscopy and heteronuclear multiple bond connectivity spectrometries.View full abstractDownload PDF (839K) -
Tozo FUJII, Tohru SAITO1990 Volume 38 Issue 7 Pages 1886-1891
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA full account is given of the synthesis and glycosidic hydrolysis of 7-alkyladenosines (4), which established an alternative synthesis of 7-alkyladenines (11). Methylation of N6-methoxyadenosine(5)with MeI in AcNMe2 at 30°C for 8h gave N6-methoxy-7-methyladenosine, which was isolated in the form of the sulfate [7a (X=1/2SO4)] in 55% yield. N6-Methoxy-N6-methyladenosine (9a) was a by-product in this methylation. Demethoxylation of 7a (X=1/2SO4)by catalytic hydrogenolysis using hydrogen and Raney Ni catalyst produced, after replacement of the anion with perchlorate ion, 7-methyladenosine perchlorate [4a (X=ClO4)] in a pure and crystalline form. 7-Ethyladenosine perchlorate [4b (X=ClO4)] was also synthesized from N6-benzyloxyadenosine (6) through a parallel route via N6-benzyloxy-7-ethyladenosine sulfate [8b (X=1/2SO4)]. On treatment with H2O at 98-100°C for 40 min, 4a (X=ClO4) and 4b (X=ClO4) furnished 7-methyladenine (11a) and 7-ethyladenine (11b) in 84% and 55% yields, respectively. Similar hydrolyses of 7a (X=ClO4) and 8b (X=1/2SO4) gave N6-methoxy-7-methyladenine (12a) and N6-benzyloxy-7-ethyladenine (12b), respectively. Catalytic hydrogenolysis of 12b using hydrogen and Raney Ni catalyst afforded 11b in 82% yield. In 0.1 N aqueous HCl at 25°C, 4a (X=ClO4) and 4b (X=ClO4) were found to undergo glycosidic hydrolysis at rates of 2.22×10-3 min-1 (half-life 5.2h) and 1.69×10-3 min-1 (half-life 6.8h), respectively. Comparison of these rate constants with those of the other three NX-methyladenosines (1-3) has revealed that the ease with which depurinylation occurs decreased in going through the series 3-(2)>7-(4a)»N6-(3)≥1-methyladenosine (1). On treatment with 1 N aqueous NaOH at 60°C for 3h, 4a (X=ClO4) was hydrolyzed to give 11a in 44% yield.View full abstractDownload PDF (1051K) -
Masateru ONO, Naoki NODA, Toshio KAWASAKI, Kazumoto MIYAHARA1990 Volume 38 Issue 7 Pages 1892-1897
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkaline hydrolysis of the ether-insoluble resin glycoside ("convolvulin") fraction, pharbitin, of the seeds of Pharbitis nil (Convolvulaceae) provided three organic acids, S-2-methylbutyric acid, (2R, 3R)-nilic acid and tiglic acid, and a new glycosidic acid named pharbitic acid B along with the known compounds pharbitic acids C and D. Pharbitic acid B was characterized as (3S, 11S)-3, 11-dihydroxyhexadecanoic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-quinovopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside. The structures of the sugar moieties of pharbitic acids C and D were revised.View full abstractDownload PDF (873K) -
Kiyoshi TOMIOKA, Hisashi KAWASAKI, Kenji KOGA1990 Volume 38 Issue 7 Pages 1898-1901
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDemethyl derivatives of steganes and deoxypodorhizon, 3, 4, 6, 7, 9, 10, 12, 13, 18, 23, were prepared by the selective demethylation of the methoxy group of steganes and deoxypodorhizon, 2, 5, 8, 11, 22. The cytotoxicity of these derivatives was evaluated against KB cell and was found not to exceed that of the parent steganes. 4-Demethyldexypodorhizon (18) was found to show more potent cytotoxicity than deoxypodorhizon (22).View full abstractDownload PDF (639K) -
Tsutomu HATANO, Shin HATTORI, Yoshitaka IKEDA, Tetsuro SHINGU, Takuo O ...1990 Volume 38 Issue 7 Pages 1902-1905
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTannins of two Acer species were investigated. Basides acertannin (1), gallotannins 2 and 3, having three and four galloyl groups on their 1, 5-anhydro-D-glucitol cores, were obtained from the leaves of Acer ginnala. The estimation of their tanning activity by the RMBG (relative affinity to methylene blue based on the affinity of geraniin) determination method revealed that the tanning activities of 2 and 3 are high, while that of 1, which has only two galloyl groups, is low. Two isomers (2a and 2b) of 2, and three isomers (3a, 3b and 3c) of 3 were respectively separated from each other after methylation. Their structures, in which all of the acyl groups (galloyl group, digalloyl group and/or trigalloyl group) are linked exclusively to O-2 and O-6 of the 1, 5-anhydro-D-glucitol core, were assigned. Fractionation of the constituents of leaves of Acer saccharum afforded two ellagitannins, geranin (10) and davidiin (11), and also chlorogenic acid and quercitrin.View full abstractDownload PDF (728K) -
Masao MIYAUCHI, Eiji NAKAYAMA, Koichi FUJIMOTO, Isao KAWAMOTO, Junya I ...1990 Volume 38 Issue 7 Pages 1906-1910
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOral delivery of 3-thiazoliomethyl cephalosporin 1 was attempted through a prodrug approach by applying thiamine chemistry. The 3-thiazoliomethyl group was modified to a ring-opened structure with no ionic charge, and the 4-carboxyl group was converted to pivaloyloxymethyl ester. Lipophilicity of the resulting derivatives (8-10) was suitable for passive absorption from the intestinal tract, and chemical stability in phosphate buffer solution (pH 6.86) was moderate. When administered orally to mice, these derivatives were mainly transformed to a novel 3-spiro cephalosporin 11, and desired reconversion to the 3-thiazoliomethyl cephalosporin was minor. Isomerization to Δ2-cephalosporin 14 was also observed. These results showed that the derivatives (8-10) tested in this study did not serve as orally active prodrugs of 3-thiazoliomethyl cephalosporin 1.View full abstractDownload PDF (776K) -
Yoshitaka OHISHI, Teruo MUKAI, Michiko NAGAHARA, Motoyuki YAJIMA, Nori ...1990 Volume 38 Issue 7 Pages 1911-1919
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-monoalkymethylidene-3-carboxymethylrhodanines (3a-u). The configuration of the 5-monoalkylmethylidene-3-carboxymethylrhodanine (3k) were examined by X-ray structure analysis and confirmed to be Z-configuration. The stereoselective reaction path was discussed. Several 5-dialkylmethylidene-3-carboxymethylrhodanines (15a-f) and alkyl-amino derivatives of 3-carboxymethylrhodanines (18a-o) were also prepared.These products were evaluated for aldose reductase-inhibitory potency and half of them exhibited valuable inhibitory potency.View full abstractDownload PDF (1183K) -
Yoshiharu MINAMITAKE, Mayumi FURUYA, Yasuo KITAJIMA, Maki TAKEHISA, Sh ...1990 Volume 38 Issue 7 Pages 1920-1926
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.View full abstractDownload PDF (1228K) -
Fumio YOSHIZAWA, Takeshi DEYAMA, Nobuo TAKIZAWA, Khan USMANGHANI, Mans ...1990 Volume 38 Issue 7 Pages 1927-1930
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA New phenylethanoid glycoside, named tubuloside E (I), and a new neolignan glycoside, dehydrodiconiferyl alcohol γ'-O-β-D-glucopyranoside (II), were isolated from the whole plants of Cistanche tubulosa (SCHRENK)HOOK. f. (Orobanchaceae), together with dehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (III), syringalide A 3'-α-L-rhamnopyranoside (IV), isosyringalide 3'-α-L-rhamnopyranoside (V), (+)-syringaresinol O-β-D-glucopyranoside (VI), (+)-pinoresinol O-β-D-glucopyranoside (VII), liriodendrin (VIII), 6-deoxycatalpol (IX), 8-epiloganic acid (X), 20-hydroxyecdysone (XI), 8-hydroxygeraniol 1-β-D-glucopyranoside (XII) and syringin (XIII). The structure of tubuloside E (I) was established as 2-(3, 4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→3)-2-O-acetyl-4-O-p-coumaroyl-β-D-glucopyranoside on the basis of chemical evidence and spectral data.View full abstractDownload PDF (721K) -
Bo-Yang YU, Yasuaki HIRAI, Junzo SHOJI, Guo-Jun XU1990 Volume 38 Issue 7 Pages 1931-1935
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven steroidal glycosides, tentatively named glycosides Ls-1, Ls-2 (1), Ls-3 (2), Ls-4 (3), Ls-5 (4), Ls-6 (5) and Ls-7 (6) were isolated from the subterranean part of Liriope spicata (THUMB.) LOUR. var. prolifera Y. J. MA (Liliaceae) and three steroidal glycosides, tentatively named glycosides Lm-1, Lm-2 (7), Lm-3 (8) were isoalted from L. muscari (DECN.) BAILEY (Liliaceae). Glycosides Ls-1 and Lm-1 were identified as so-called β-sitosterol β-D-glucopyranoside. The structures of eight glycosides (1-8) were established as (25S)-ruscogenin 1-O-β-D-fucopyranosido-3-O-α-L-rhamnopyranoside (1)(=glycoside B from L. platyphylla WANG. et TANG.), (25S)-ruscogenin 1-O-β-D-xylopyranosido-3-O-α-L-rhamnopyranoside (2), (25S)-ruscogenin 1-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranoside (3), (25S)-ruscogenin 1-O-[(2-O-acetyl)-α-L-rhamnopyranosyl(1→2)][β-D-xylopyranosyl(1→3)]-β-D-fucopyranoside (4), (25S)-ruscogenin 1-O-[(3-O-acetyl)-α-L-rhamnopyranosyl(1→2)][β-D-xylopyranosyl(1→3)]-β-D-fucopyranoside (5), yamogenin 3-O-[α-L-rhamnopyranosyl(1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside (6), ruscogenin 1-O-β-D-glucopyranosyl(1→2)-β-D-fucopyranoside (7) and ruscogenin 1-O-[β-D-glucopyranosyl(1→2)][β-D-xylopyranosyl(1→3)]-β-D-fucopyranoside (8), respectively.View full abstractDownload PDF (903K) -
Yoshiki MINO, Hidetaka TORII, Nagayo OTA1990 Volume 38 Issue 7 Pages 1936-1941
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInorganic constituents of many Coptidis Rhizoma and Phellodendri Corte (28 and 37 samples, respectively;almost all obtained commercially in Osaka market) were investigated using energy-dispersive X-ray fluorescence spectrometry.The results can be summarized as follows : (1) Coptidis Rhizoma contained Zn, Mn, Cu, and S at higher levels, and Ca and Sr at lower levels than those of Phellodendri Cortex. The analysis of Zn and Ca contents provided almost perfect distinction between the two drugs.(2) Coptidis Rhizoma contained Zn at high levels, and the contents of Zn, Mn, and Rb were dependent on the producing district(Japan or China).(3) The metals profile of each crude drug provides valuable information regarding the identification of not only the kind of drug but also the producing district or the botanical origin.View full abstractDownload PDF (724K) -
Takashi HAKAMATSUKA, Hiroshi NOGUCHI, Yutaka EBIZUKA, Ushio SANKAWA1990 Volume 38 Issue 7 Pages 1942-1945
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLiquiritigenin and isoliquiritigenin were converted into daidzein by a microsomal fraction of cell suspension cultures of Pueraria lobata OHWI, which had been treated with an endogenous elicitor prepared by hydrolysis of their own cell walls with a fungal endopolygalacturonase. Competitive experiments with [3H]flavanone and [14C]chalcone as the substrates for isoflavone synthase revealed that flavanone is the true substrate for this enzyme reaction and the possible role of chalcone in the reaction is excluded.View full abstractDownload PDF (677K) -
Yasuhisa FUJIBAYASHI, Kazuya MATSUMOTO, Yasushi ARANO, Yoshiharu YONEK ...1990 Volume 38 Issue 7 Pages 1946-1948
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS^<62>Cu-Labeling of human serum albumin-dithiosemicarbazone (HSA-DTS) conjugate was performed using a newly developed 62Zn/62Cu generator system. HSA-DTS was easily labeled with 62Cu, by simple mixing with 62Cu-generator eluate. In vivo blood clearance of 62Cu-HSA-DTS was similar to 131I-HSA, indicating the high applicability of 62Cu-HSA-DTS as a method for plasma volume measurement. In a positron emission tomography study of a dog, a clear plasma pool image of the head region was obtained.View full abstractDownload PDF (732K) -
Hiroshi HOSODA, Ken OSANAI, Ikuo FUKASAWA, Toshio NAMBARA1990 Volume 38 Issue 7 Pages 1949-1952
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of the 3- and 21-glucuronides of allotetrahydrocortisol (allo-THF) and allotetrahydrocortisone (allo-THE) is described. 5α-Dihydrocortisol (5) was prepared by selective hydrogenation of 21-acetoxy-3, 11β, 17α-trihydroxy-3, 5-pregnadien-20-one 3-ethyl ether (3), followed by acid hydrolysis and saponification. When 5α-dihydrocortisol 21-tetrahydropyranyl ether (6) was treated with potassium tri-sec-butylborohydride in tetrahydrofuran under mild conditions, regioselective and stereoselective reduction at C-3 took place to give allo-THF 21-tetrahydrophyranyl ether (7). This compound was converted into the 3- and 21-monoacetates of allo-THF and allo-THE, key intermediates. Introduction of the glucuronyl residue at C-3 or C-21 was carried out by means of the Koenigs-Knorr reaction. Prior to saponification yielding the 3-glucuronides (20, 23), the alkali-sensitive ketol side chain at C-17 was protected as 20-semicarbazones.View full abstractDownload PDF (753K) -
Noriko MOTOHASHI, Yoshiko NAKAMICHI, Itsuhiko MORI, Hitoshi NISHIKAWA, ...1990 Volume 38 Issue 7 Pages 1953-1956
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe concentration and degradation of hyaluronic acid in the synovial fluid of carrageenin-induced arthritic joints of rabbits was studied. A 0.5-ml volume of 1% λ-carrageenin was intra-articularly injected three times into a right knee joint, and saline into a left. After 5 d from the last injection, inflammatory changes were observed in the synovial membrane and synovial fluid, but not in the articular cartilage. In the inflammatory synovial fluid, lipid peroxide content, phosphatase activity and cell counts were significantly increased, but the copper concentration was not changed. Concentration of polymeric hyaluronic acid and total hyaluronic acid were determined by high-performance liquid chromatography using gel-permeation columns. Total hyaluronic acid was appreciably decreased in the inflammatory fluid. The polymeric hyaluronic acid determined was 38% of the toal hyaluronic acid in the inflammatory fluid and 74% in the control fluid. This suggests that in the inflammatory fluid, molecular weights of hyaluronic acid are distributed in the broader range. The concentration of chondroitin sulphates was similar in both the inflammatory fluid and the control fluid, but the content ratio of chondroitin sulphates to hyaluronic acid was higher in the inflammatory fluid. In the inflamed synovial membrane, synthesis of hyaluronic acid as measured by incorporation of [14C]glucosamine into glycoconjugates was increased by about twice that in the control membrane.View full abstractDownload PDF (775K) -
Hiroshi NAKAO, Takao NAGOYA, Akio IWASAKI, Makoto SUDA, Yukio HATTORI, ...1990 Volume 38 Issue 7 Pages 1957-1960
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe developed a sandwich enzyme-linked immunosorbent assay (ELISA) system for calphobindin I (CPB-I), a new placental coagulation inhibitor, using two monoclonal antibodies. This ELISA system can detect CPB-I at concentrations of between 0.4 and 25 ng/ml in buffer and allow almost quantitative determination of it in human plasma. Using this ELISA system, CPB-I levels in many kinds of specimens were measured. Levels in the plasma and urine of women were as low as 10 ng/ml, and no significant differences were observed throughout the trimesters of pregnancy and during different stages of the menstrual cycle. Toxemic patients were slightly higher in CPB-I levels than normal pregnant women, and levels in body fluids such as the amniotic fluid, saliva, milk, ascites, and semen were higher than those in the plasma. The high levels of CPB-I were found, being in the order of μg/ml, in the ascites of carcinomatous peritonitis as well as seminal plasma. Measurements of the levels in ovarian follicular fluid samples at different stages of the menstrual cycle showed that those in the immature and atretic stages were higher than those in mature stages. CPB-I levels in many types of cultured human cells ranged from 0.023 to 10.30 μg/mg protein, and levels in cultured human lymphocytes were less than those in other types of cells measured. Little of this inhibitor was secreted into media from cultured human lymphocytes, and it was found in all measured tissues of Macacus irus at levels ranging from 0.232 to 1.557 μg/mg protein. From these results, it was suggested that CPB-I might be a ubiquitous protein in the body that has an important physiological role.View full abstractDownload PDF (635K) -
Jian-Guo HU, Tetsuo YOKOYAMA, Tsunehiro KITAGAWA1990 Volume 38 Issue 7 Pages 1961-1965
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of several conditions for the immunization of mice was studied using an aliquot of a viomycin (VM) protein conjugate as the common primary or booster antigen. Responses of the mice were assessed by measuring mouse serum levels of total immunoglobulin G (IgG) and anti-VM antibody respondes using the newly improved two assay methods. The choice of route was found to be a very important factor in immunization and intraperiotoneal injection was the most optimal among the four routes studied. The effect of the concentration of Mycobacteria in Freund's complete adjuvant (FCA) was also studied, and it was found that a diluted FCA was more effective that a commercial FCA. The effect of the controlled release of the antigen was studied and three important phenomena were observed : The mice immunized by the mini-osmotic pump-aided controlled release of the antigen responded with similar small amounts of both total IgG and anti-VM antibody regardless of the presence or absence of FCA in the antigen; emulsifiing the antigen with FCA was a very important condition for the effective elicitation of the specific antibody; a mixture of antigen and FCA without emulsifying produced little specific antibody and a large amount of total IgG. The more effectively immunizated mice responded with a larger decrease in body weight soon after the primary injection.View full abstractDownload PDF (792K) -
Ryoko GONDA, Masashi TOMODA, Noriko SHIMIZU, Mieko KANARI1990 Volume 38 Issue 7 Pages 1966-1969
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn acidic polysaccharide, named eucomman A, was isolated from the dried bark of Eucommia ulmoides OLIV. It was homogeneous on electrophoresis and gel chromatography, and showed significant reticuloendothelial system-potentiating activity in a carbon clearance test. It is composed of L-arabinose : D-galactose : D-glucose : L-rhamnose : D-galacturonic acid in the molar ratio of 8 : 6 : 4 : 5 : 8 in addition to small amounts of peptide moiety. Its molecular mass was estimated to be 6.0×104. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies enabled elucidation of its structural features.View full abstractDownload PDF (642K) -
Masayoshi TAKEUCHI, Nachiko TAKAI, Naoki ASANO, Yukihiko KAMEDA, Katsu ...1990 Volume 38 Issue 7 Pages 1970-1972
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree pseudo-aminosugars, validamine, valienamine and valiolamine, produced by Streptomyces hygroscopicus subsp. limoneus showed potent inhibitory action on rat small intestinal carbohydrase activities such as sucrace, maltase, glucoamylase, isomaltase and trehalase activities, but negligible action on lactase activity and pancreatic α-amylase activity. Where inhibition was seen, kinetic analysis showed fully competitive inhibition of the carbohydrase activities by all three inhibitors. Valiolamine has more potent carbohydrase inhibitory activity than validamine or valienamine, and the apparent Ki values of valiolamine for sucrase, maltase, glucoamylase, isomaltase and trehalase activities were 3.2×10-7, 2.9×10-6, 1.2×10-6, 9.1×10-7 and 4.9×10-5M, respectively, which are 10-5 to 10-3 times smaller than the apparent Km values.View full abstractDownload PDF (567K) -
Eiji YUKAWA, Shun HIGUCHI, Toshinobu AOYAMA1990 Volume 38 Issue 7 Pages 1973-1976
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRoutine clinical pharmacokinetic data collected from outpatients receiving phenytoin (PHT) were reanalysed to estimate population pharmacokinetic parameters. There were 756 steady-state PHT concentrations and associated dosage rates (mg/d) from 334 outpatients. The data were analysed using nonlinear effects model (NONMEM), a computer program designed for population pharmacokinetic analysis that allows pooling of data from many individuals. The influence of weight, co-anticonvulsants on the maximum elimination rate (Vm) and age, co-anticonvulsants on the Michaelis-Menten constant (Km) and the influence of dosage form on the bioavailability (F) of PHT were investigated.The Vm and Km of a 60 kg adult outpatient treated with PHT alone were estimated to be 325 mg/d and 2.41 μg/ml, respectively, while for a same size individual taking PHT with co-anticonvulsants respective estimates were 351 mg/d and 3.18 μg/ml. The parameter of a power function of weight was estimated to adjust Vm for body size. The best function adjusts Vm in proportion to weight to the 0.737 power. The Km for patients less than 15 years old was 24.8% less than that of adults. Assuming the F of PHT to be 1 in patients prescribed a tablet, the F value in patients prescribed a powder was [1-exp(-9.92/Dij)]; Dij is the daily dose of PHT for the ith Cpss in the jth patients (mg/kg/d).View full abstractDownload PDF (752K) -
Keijiro TERASHITA, Masaya KATO, Atsuo OHIKE, Kei MIYANAMI1990 Volume 38 Issue 7 Pages 1977-1982
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA granulation experiment was conducted using different granulator and formulation. The purpose of the experiment was to clarify the granulation end-point to gain high yields of spherical, well-compacted granules and fine granules, and to investigate the agitation-granulating process. The fluctuation of electric-power consumption was continuously measured during the granulation operation, and it was determined that measurement of power consumption was helpful for determining the granulation process and granulation end point.One of the results of the experiment was that the granulation process was divided into four phases, and at the initial stage of phase IV high yields of spherical, well-compacted granules and fine granules are possibly produced (granulation end-point). It was found that the granulating mechanisms in each of the phases is not affected by the use of different agitation granulators, formulations, or the binder addition time adopted. The specific binder addition time and granulator model that produced high yields of granules and fine granules were identified.View full abstractDownload PDF (1252K) -
Hypoglycemic Effect of Intestinally Administered Monosaccharide-Modified Insulin Derivatives in RatsMakoto HAGA, Katsumi SAITO, Takahiro SHIMAYA, Yukiko MAEZAWA, Yuriko K ...1990 Volume 38 Issue 7 Pages 1983-1986
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of the modification of insulin (INS) with p-succinylamidophenyl (SA)-α-D-glucopyranoside (SAPG), SA-α-D-mannopyranoside and SA-α-L-arabinopyranoside on the enzymatic degradation and the hypoglycemic effect in rats was studied. When SAPG-INS was administered intraintestinally in the absence of bile and pancreatic juice, blood glucose level decreased to 56% of initial value. Other monosaccharide derivatives were less effective than SAPG-INS. The digestion of monosaccharide derivatives by pepsin and chymotrypsin indicated that the resistance of insulin to enzymatic degradation was increased by its modification with monosaccharide. One possibility for the hydroglycemic effect of SAPG-INS could be the increased resistance of insulin to enzymatic degradation as a result of its modification with monosaccharide.View full abstractDownload PDF (758K) -
Ryuzo ISHINO, Hiroyuki YOSHINO, Yoshiyuki HIRAKAWA, Kazuo NODA1990 Volume 38 Issue 7 Pages 1987-1992
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo examine the influence of tabletting speed on compactibility and compressibilty under high speed compression, two direct compressible powders, α-lactose monohydrate and microcrystalline cellulose of different particle size ranges were compressed using an instrumented rotary press with varying tabletting speed and compression force. The maximum applied force and total time during compression (contact time) were determined from a time-force profile, and the relation between these parameters and properties of compacts was examined. For all lactose tablets, the porosity and tensile strength of compacts were less affected by compression rate though they depended on the applied force. However, the properties of microcrystalline cellulose tablets were varied depending on the tabletting speed in addition to the applied force. In an attempt to quantitatively evaluate the effect of compression rate on the compactibility, an empirical equation was derived from the numerical analysis of the experimental data. The compactibility parameters deduced from the equation well elucidated the effect of tabletting speed on the properties of microcrystalline cellulose tablets and lactose tablets made of various particle size powders.View full abstractDownload PDF (836K) -
Kozo TAKAYAMA, Meiko HIRATA, Yoshiharu MACHIDA, Tomoaki MASADA, Takano ...1990 Volume 38 Issue 7 Pages 1993-1997
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bioadhesion property of tablets consisting of chitosan (CS) and sodium hyaluronate (HA) was investigated using a lyophilized porcine dermis as a model of mucous membrane. Release phenomena of brilliant blue FCF (BBL) from the CS-HA tablets were also studied. BBL was employed as a model compound of water-soluble drugs. Strong adhesion force were observed when the tablets were prepared from HA alone or a physical mixture of CS and HA. The adhesion of CS tablets was also obtained but it was rather weak. No effect of pH values in the media was observed on the adhesion force in these tablets. On the other hand, the release rate of BBL from CS-HA tablets was greatly affected by the change of the polymer mixing ratio, suggesting a possible interaction between CS and HA in the tablet following water penetration into the tablet.View full abstractDownload PDF (800K) -
Tatsuo SUGIOKA, Toshikazu ASANO, Yuji CHIKARAISHI, Emi SUZUKI, Akimits ...1990 Volume 38 Issue 7 Pages 1998-2002
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stability and degradation pathways of a new semi-synthetic cephalosporin, 1-[[(6R, 7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6, 7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime) sulfate (cefpirome sulfate, HR 810), were studied.Cefpirome in various buffer solutions was allowed to stand at 40°C and its degradation patterns were investigated by high performance liquid chromatography. Cefpirome was stable in the region of pH 4-7 and slightly unstable beyond this range.In aqueous solution from the neutral to alkaline regions, the produced degradation products were : 1-[[(6R, 7S)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6, 7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime)(epi-cefpirome); 1-[[(6R, 7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-hy]methyl]-6, 7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime)(Δ2-cefpirome); 2-[[(2-amino-4-thiazolyl)((Z)-methoxyimino)acetyl]amino]acetaldehyde; and 6, 7-dihydro-5H-1-pyrindine. On the other hand, 1-[[(6R, 7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6, 7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(E)-(O-methyloxime) (anti-cefpirome), 2-[[(2-amino-4-thiazolyl)-((Z)-methoxyimino)-acetyl]aminomethyl]-1, 2, 5, 7-tetrahydro-7-oxo-4H-furo[3, 4-d]-[1, 3]thiazine, and 6, 7-dihydro-5H-1-pyrindine were produced in strongly acidic solution or under irradiation by artificial sunlight.View full abstractDownload PDF (799K) -
Tsutomu KONNO1990 Volume 38 Issue 7 Pages 2003-2007
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFlufenamic acid (FFA) was mixed with magnesium aluminum silicate (MAS) at a reduced pressure of about 10 to 50 mmHg employing a commercial mixer for pharmaceutical production. An amorphous state of FFA in the mixture was efficiently achieved with this equipment, and the dissolution of FFA was enhanced in comparison with that of the physical mixture. Effects of the conditions of mixing, such as pressure, temperature and rotating speed, on dissolution of FFA were determined. Through stability tests at 40°C under both dry and humid conditions, no change in dissolution profiles was recognized in a 5% FFA mixtures stored under any conditions. On the other hand, decreases in dissolution behavior were observed in 10% and 20% FFA mixtures when they were stored under humid conditions. These results suggested that humidity should be avoided during the storage of amorphous mixtures of FFA with MAS for production purposes.View full abstractDownload PDF (868K) -
Yayoi HAYASHI, Jun WATANABE1990 Volume 38 Issue 7 Pages 2008-2011
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of 5-fluorouracil (5-FU) concentration in the perfusate on the salivary excretion of 5-FU was investigated in the rat mandibular gland perfused with modified Ringer solution containing pilocarpine (10 μM). The saliva to venous-effluent concentration ratio (S/E ratio) of 5-FU increased gradually during the perfusion. The 5-FU concentration in the perfusate ranging from 10 to 200 μg/ml caused elevation in the mean value of S/E ratio. This non-linearity suggested that the present perfusion method would be useful to further investigation for the mechanism of salivary excretion of 5-FU, since the tendency of the non-linearity was similar to that in in vivo studies as reported previously. The salivary flow rate declined with time, and the greater mean value of the flow rate was obtained during perfusion with the perfusate containing the lower level of 5-FU. Statistically significant correlation was found between the S/E ratio of 5-FU and salivary flow rate (p<0.01). Therefore, in the perfused rat mandibular gland, it was concluded that 5-FU itself had an influence on the salivary excretion of 5-FU via dicreasing salivary flow rate. On the other hand, the salivary clearance of 5-FU showed no distinct increase and/or decrease not only with time but also with the change of 5-FU concentration in the perfusate. It seems to result from the cancellation of the increased S/E ratio of 5-FU by the decreased salivary flow rate in perfused rat mandibular gland.View full abstractDownload PDF (663K) -
Mitsutaro AKAO, Keiko KURODA1990 Volume 38 Issue 7 Pages 2012-2014
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inhibitory effect of fumaric acid (FA) on hepatocarcinogenesis was examined in mice fed thioacetamide (TAA). A group of male ICR mice was fed TAA at a level of 0.035% in the diet for 40 weeks and then fed a basal diet for 48 weeks. Hepatic tomors developed in 11 of the 24 animals of this group and they were diagnosed as hepatocellular carcinomas. However, cirrhotic lesions and the enlargement of hepatocyte nucleoli were not as marked in mice as in previous findings in rats fed TAA. The effect of FA on the carcinogenesis was examined in a group of mice fed this compound at a level of 1% in a basal diet after ingestion of TAA. The inhibitory effect of FA on TAA carcinogenesis was so marked that no hepatic carcinomas were found in any of the 15 animals fed FA in combination with TAA.View full abstractDownload PDF (834K) -
Osamu MATSUMOTO, Hideki MASUDA, Tooru TAGA, Yoshihiro KURODA, Katsunos ...1990 Volume 38 Issue 7 Pages 2015-2017
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 600 MHz 1H-nuclear magnetic resonance spectra of a mixed aqueous solution of typsin and a synthesized trypsin inhibitor, 4-[4-(N, N-dimethylcarbamoylmethoxycarbonylmethyl)phenoxycarbonylphenyl]-guanidinium methanesulfonate(FOY-305) were measured. Signals assigned to the inhibitor protons indicated that the hydrated fragment of the inhibitor formed a complex with trypsin. The signal change during 4 h of incubation at 37°C was interpreted as reflecting a successive process of the partial release of the fragment and its weak recombination with the enzyme around the active site. The result is consistent with the disorder of the fragment in the crystal structure of the inhibitor : trypsin complex.View full abstractDownload PDF (459K) -
Norimitsu HAMAMICHI, Tadashi MIYASAKA1990 Volume 38 Issue 7 Pages 2018-2019
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Dicyanomethylene-9-tetrahydrofuranylpurine (4), which was obtained by the reaction of 9H-1, 6-dihydropurine-Δ6, α-propanedinitrile (3) with 2, 3-dihydrofuran, has been catalytically hydrogenated to the α-(aminomethylene)-9-(tetrahydrofuran-2-yl)-9H-purine-6-acetonitrile (5) in good yield using N, N-dimethylformamide-benzene as a solvent over Pd-C under medium pressure. Substitution of 5 with amines gave the corresponding alkylaminomethylene purines (6 and 7). Reaction of 5 with hydrazine gave the pyrazole derivative (8).View full abstractDownload PDF (438K) -
Chung-gi SHIN, Nobuyuki TAKAHASHI, Yasuchika YONEZAWA1990 Volume 38 Issue 7 Pages 2020-2023
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious N-benzyloxycarbonyl-α-dehydroamino acid methyl esters were newly synthesized by the condensation of α-oxocarboxylic acids with benzyl carbomate followed by methyl esterfication. Others were obtained by the Wittig-Horner reaction of aldehydes with diethoxyphosphinylglycine and by the base-catalyzed β-elimination of β-acetoxy or β-halo-α-amino acids.View full abstractDownload PDF (635K) -
Hiroyoshi YAMAZAKI, Hiroshi HORIKAWA, Takashi NISHITANI, Tameo IWASAKI1990 Volume 38 Issue 7 Pages 2024-2026
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically pure amines were synthesized effectively by Lewis acid-catalyzed triethylsilane reduction of N-acyl-α-methoxyalkylamines which were readily obtained by anodic oxidation of N-acyl-α-amino acids. This method was also applied to the conversion of an N-acylpeptide into the corresponding optically pure amine derivative.View full abstractDownload PDF (625K) -
Seiji MORITA, Kenji OTSUBO, Minoru UCHIDA, Shigekatsu KAWABATA, Hisash ...1990 Volume 38 Issue 7 Pages 2027-2029
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites of 9-fluoro-6, 7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H, 5H-benzo[i, j]quinolizine-2-carboxylic acid (OPC-7251) (1), which has a potent antiabacterial activity against gram-positive bacteria, characteristically Propionibacterium acnes, were synthesized to confirm their structures and to examine their antibacterial activity. The structures of three major metabolites (2, 3a and 4) were identified by means of comparison with the synthetic compounds. The antibacterial activity of the metabolites (2, 3a and 4) was found to be lower than that of 1.View full abstractDownload PDF (534K) -
Kazuhiro MATSUMOTO, Ryoji KASAI, Kazuhiro OHTANI, Osamu TANAKA1990 Volume 38 Issue 7 Pages 2030-2032
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom fruits of Siraitia grosvenori, a Chinese medicinal plant, a new minor glycoside and four known minor cucurbitane glycosides, siamenoside I (sweet), 11-oxo-mogroside V (sweet), and mogrosides IIE and IIIE (both tasteless) were isolated together with mogrosides IV and V (both sweet) previously isolated from this fruit by Arihara et al. Structure of the new testeless glycoside called mogroside III was elucidated as 3-O-β-D-glucopyranosyl- 24-O-β-gentiobiosyl-mogrol. The relative sweetness of siamenoside I to sucrose was estimated ×563, making this the sweetest compound among the cucurbitane-glycosides so far isolated. The structure-taste relationship of cucurbitane-glycosides is also described.View full abstractDownload PDF (538K) -
Johji YAMAHARA, Hisashi MATSUDA, Yoshikazu NAITOH, Hajime FUJIMURA, Yo ...1990 Volume 38 Issue 7 Pages 2033-2034
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe screening test was carried out to identify new drugs from natural products for the KCN-induced anoxia model in mice. Acetone extract of Atractylodis Lanceae Rhizoma (Atractylodes lancea DC. var. Chinensis KITAMURA) had a significant effect in the KCN-induced anoxia model and therefor the extract was selected for further study in order to identify the active principles. The result showed that β-eudesmol was the active component in Atractylodis Lanceae Rhizoma.View full abstractDownload PDF (398K) -
Miki NIIKAWA, Yoshimichi SAKAI, Youki OSE, Takahiko SATO, Hisamitsu NA ...1990 Volume 38 Issue 7 Pages 2035-2039
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBoiling-water extract of Korean-Saiko (Bupleuri Radix, from South Korea, Bupleurum falcatum L.) enhanced the mutagenic activity of Trp-P-1, Trp-P-2 and benzo[a]pyrene with S9mix. The boiling-water extract was fractionated with ether and then n-BuOH. Both the ether and the n-BuOH fractions also enhanced mutagenicity of Trp-P-1, respectively. The n-BuOH fraction was separated into seven fractions by silica gel chromatography and the chloroform eluate had the strongest enhancing effect on the mutagenic activity of Trp-P-1 with S9mix.The chloroform eluate fraction was further separated into five by thin-layer chromatography. Two of the spots had the strongest enhancing effect on the mutagenic activity of Trp-P-1.Since saikosaponin is a well known component in Bupleuri Radix, the effects of its existence were tested and saikosaponins a and c were found. The enhancement activity of saikosaponin a was very weak. The effective comoponents are now being studied.View full abstractDownload PDF (674K) -
Mitsuteru NUMAZAWA, Kumiko HOSHI, Tomomi KONNO, Masao NAGAOKA1990 Volume 38 Issue 7 Pages 2040-2042
Published: July 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS16α-Hydroxyandrost-4-ene-3, 17, 19-trione (10) was synthesized from the 16α-hydroxy-6β, 19-epoxy-17-one 3 via protection of the 16α-hydroxy function as its tert-butyldimethylsilyl ether or acetate. Reductive cleavage of the epoxy ring of the silyl ether 4 or the acetate 5 with zinc dust gave the 19-alcohol 6 or 7, which was treated with pyridinium dichromate or Jones reagent, respectively, and then hydrolyzed with diluted sulfuric acid, yielding the desired steroid 10. 3β, 16α-Dihydroxyandrost-5-ene-17, 19-dione (14) was also synthesized from 5α-bromo-3β, 16α-diacetoxy-6β, 19-epoxyandrostan-17-one (11) through the intermediates 12 and 13 with the 3β- and 16α-hydroxy functions protected as their acetates in a reaction sequence similar to that above.View full abstractDownload PDF (557K)