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Volume 35, Issue 3
Displaying 1-50 of 58 articles from this issue
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CHIKAKO YOMOTA, MASAYUKI NAKAGAKI1987 Volume 35 Issue 3 Pages 933-940
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe cation binding behavior of arabate was investigated by conductivity measurements with reference to the various colligative properties of arabate reported previously. The equivalent conductance of arabic anion, Λp, was found to be about 6 (Ω-1.cm-1.eq-1) from the conductivity titration curves of arabic acid with tetra-n-butylammonium hydroxide (TBA-OH). Using the value of Λp = 6, cation binding of arabate was estimated by the conductivity measurement of TBA-arabate at a constant concentration of 1.2 × 10-2 (eq/kg) in the presence of various added salts, and the binding curves were found to be of Langmuir type. Since the saturated amounts of cation binding, x∞ were observed to be similar to each other among cations of the same valency, since they increased with the valence number of cations, the interactions of arabate with cations were suggested to be due to electrostatic force. The present results are discussed in terms of the estimation methods of cation binding behavior of arabate.View full abstractDownload PDF (1097K) -
MITSUO NAKAJIMA, MINORU TSUDA, SETSUKO OIKAWA1987 Volume 35 Issue 3 Pages 941-947
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSAb initio molecular orbital configuration interaction calculations were carried out on the intrinsic reaction coordinate (IRC) path of the reaction CH4+ O (1D) →CH3OH. The oxygen atom (1D) approaches methane along the C3 rotational axis of C3v, symmetry on the lowest potential energy path of the ground state. The ground state and four kinds of excited states of methanol originate from CH4+ O (1D). The reaction system of CH4+ O (1S) generates a higher excited state than those from CH4+ O (1D). It was confirmed that the ground state function along the IRC path can be approximately expressed by the Hartree Fock function near the saddle point. The increase of antibonding δ character with the C-O bond formation is the origin of the elevation of energies and the splitting of the five excited states.View full abstractDownload PDF (963K) -
KOICHI KOJIMA, KAZUO KOYAMA, SHIGEO AMEMIYA, SHINICHI SAITO1987 Volume 35 Issue 3 Pages 948-956
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA prostacyclin analogue, dl-3-oxa-9 (Ο)-methano-Δ6 (9α) -prostaglandin I1 (1a), has been synthesized. The key step for this synthesis is a new, one-step conversion reaction of the (hydroxymethyl) cyclopropylketone group in 8 and 21 to the γ, δ-unsaturated ketone 9 and 22, respectively, with iodotrimethylsilane.View full abstractDownload PDF (1571K) -
HIDEYUKI HARUYAMA, SADAO SATO, KAYOKO KAWAZOE, MICHIO KONDO1987 Volume 35 Issue 3 Pages 957-969
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSIn addition to variable-temperature experiments and the analysis of vicinal coupling constants, a quantitative treatment of T1 values and nuclear Overhauser effect (NOE) factors was applied to the conformation analysis of novel heterocycles, substituted 4, 1-benzothiazepine (1) and 5, 1-benzothiazocine (2). The most probable conformations of the seven-and eight-membered rings of 1 and 2, respectively, could be distinguished by comparing the observed T1 values and NOE factors with those calculated for several possible conformers.
By the quantitative analysis of T1 values at-90.2 °C and at room temperature (24.5°C), 1 was found to be in an equilibrium state of rapid ring inversion between two chair forms in the ratio of 0.7 : 0.3 (at 24.5 °C), and the major conformer was the chair form with 5-methyl group equatorial.
The X-ray analysis of 2 showed that the eight-membered ring adopted a boat-boat like conformation in the crystal. Although this conformation seemed to be consistent with most of the observed relaxation data obtained in solution, the significant shielding effect expected on H4a was not observed. By a systematic search of the conformers, a boat-chair like conformer was found to satisfy all the observed relaxation and shielding data.View full abstractDownload PDF (1682K) -
KOTOMI KATSUMI, TOSHIO OKANO, YURIE ONO, EMIKO MAEGAKI, KUMIKO NISHIMU ...1987 Volume 35 Issue 3 Pages 970-979
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFour vitamin D2 and D3 metabolites, 24, 25-dihydroxyvitamin D2 (8), 24, 25-dihydroxy-22-dehydrovitamin D3 (10). 25-hydroxy-24-oxo-22-dehydrovitamin D3 (12) and 22, 24, 25-trihydroxy-vitamin D3 (14), were synthesized from ergosterol (1) via the hydroxyketone (4) as a common key intermediate.View full abstractDownload PDF (1488K) -
MIYOJI HANAOKA, MITSURU INOUE, NOBUYUKI KOBAYASHI, SHINGO YASUDA1987 Volume 35 Issue 3 Pages 980-985
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA formal synthesis of (±) -cis-alpinigenine (3) and (±) -cis-alpinine (4) was achieved by conversion of palmatine (7) into the key intermediate, benzindenoazepine (16), via the ring D-inverted 2, 3, 11, 12-tetraoxygenated phenolbetaine (14) and the 8, 14-cycloberbine (15) through photooxygenation, photochemical valence isomerization, and regioselective C-N bond cleavage of 15 as crucial reactions.View full abstractDownload PDF (1020K) -
SUGURU TAKATSUTO, NOBUO IKEKAWA1987 Volume 35 Issue 3 Pages 986-995
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSIn order to investigate the regioselectivity of Baeyer-Villiger oxidation, thirty 5α-cholestan-6- one derivatives with various substituents (methyl, hydrogen, acetoxymethyl, methoxy, acetyloxy, benzoyloxy, trifluoroacetyloxy, p-toluenesulfonyloxy) at the C-1, C-2, or C-3 position were synthesized from cholesterol. The 6-oxo functional group of 5α-cholestan-6-one derivatives was introduced via hydroboration. The 3β-derivatives were readily obtained by using the native 3β- hydroxyl group of cholesterol. The 3α-isomers were obtained by inversion of the configuration of the 3β-tosylate 24 with tetra-n-butylammonium acetate in refluxing 2-butanone. The 2β-isomers were derived from the 2-ene 43 by bromohydrination, LiAlH4 reduction, and esterification. The 2β- to 2α-hydroxyl group inversion was achieved by Birch reduction of the 2-oxo steroid 51. The 1α-derivatives were derived from the known 6β-acetoxy- 1 α-hydroxy-5α-cholest-2-ene (57).View full abstractDownload PDF (1723K) -
NORIKAZU TAMURA, HIDEAKI NATSUGARI, YASUHIKO KAWANO, YOSHIHIRO MATSUSH ...1987 Volume 35 Issue 3 Pages 996-1015
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA new type of 5, 6-cis-carbapenems (racemic) having a sulfonyl group in the C-6 side-chain were synthesized by employing the synthetic methodology reported in our previous papers, and an alternative stereocontrolled synthesis of these 5, 6-cis-carbapenems was achieved starting from 8-oxo-7-azabicyclo [4.2.0] oct-3-ene (14) via an intramolecular aldol condensation as the key step. Chiral 5, 6-cis-carbapenems were also synthesized from (1S, 6R) -8-oxo-7-azabicyclo [4.2.0] oct-3-ene (29), which was derived from cis-1, 2, 5, 6-tetrahydrophthalic anhydride. The carbapenems thus obtained proved to be highly stable to the mouse kidney homogenate, and most of them showed good antibacterial activity as well as potent β-lactamase inhibitory activity.View full abstractDownload PDF (2987K) -
MOHAMMED EKRAMUL HAQUE, TOHRU KIKUCHI, KIMIHIRO KANEMITSU, YOSHISUKE T ...1987 Volume 35 Issue 3 Pages 1016-1029
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSRegioselective thioacylation of some non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, Me β-D-Xy1) was examined by the dibutyltin oxide method, using phenoxythiocarbonyl chloride as the thioacylating agent. This method gave the mono-thionocarbonates regioselectively in high yields. Acetylation of these thionocarbonates followed by deoxygenation with tributyltin hydride smoothly gave the corresponding deoxy derivatives, except for the primary thionocarbonates. Similar treatment of the pyranosides that have a cis-vicinal glycol (Me α-D-Gal, Me β-D-Gal, Me β-L-Ara, and Ph α-L-Ara) led to the formation of cyclic thionocarbonates, which on acetylation followed by olefination with trimethyl phosphite afforded the unsaturated derivatives in satisfactory yields. On deacetylation and subsequent hydrogenation over platinic oxide, they gave the corresponding dideoxy derivatives quantitatively. The compounds thus prepared were identified by analyses of their proton and carbon-13 nuclear magnetic resonance spectra.View full abstractDownload PDF (2221K) -
KOUHEI TOYOOKA, YASUSHI KAWASHIMA, SEIJU KUBOTA1987 Volume 35 Issue 3 Pages 1030-1035
Published: March 25, 1987
Released on J-STAGE: February 12, 2010
JOURNAL FREE ACCESSThe synthesis of 2-substituted 5- (1-oxido-4-pyridy1) - (4a-10a) and 5- (1-oxido-2-pyridyl) -1, 3, 4-thiadiazole derivatives (4b-10) by substitution reaction of 5- (1-oxido-4-pyridyl) - (3a) and 5- (1-oxido-2-pyridyl) -2-methylsulfonyl-1, 3, 4-thiadiazole (3b) is described. 5- (1-Oxido-4-pyridyl) - (9a) and 5- (1-oxido-2-pyridyl) -1, 3, 4-thiadiazole (9b) could be reduced with sodium dithionite to 2- (4-pyridyl) - (11c) and 2- (2-pyridyl) -1, 3, 4-thiadiazole (11d)View full abstractDownload PDF (754K) -
YOSHINOBU MUROFUSHI, MISAKO KIMURA, YASUTERU IIJIMA, MITSUO YAMAZAKI, ...1987 Volume 35 Issue 3 Pages 1036-1043
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSMono-, di-or triacylated griseolic acid derivatives were synthesized by selective acylation or by selective hydrolysis of the polyacylated derivatives. The inhibitory activities of these compounds against adenosine 3', 5'-cyclic monophosphate or guanosine 3', 5'-cyclic monophosphate phosphodiesterase were investigated to clarify the structure activity relationship. Acylation of the amino group of the adenine moiety greatly reduced the inhibitory activity. On the other hand, acylation of the hydroxy groups at the 7'- and 2'-position had relatively little effect on the inhibitory activity.View full abstractDownload PDF (1498K) -
KOICHI KAWASAKI, TOSHIKI TSUJI, MITSUKO MAEDA, TATSUYA MATSUMOTO, KATS ...1987 Volume 35 Issue 3 Pages 1044-1048
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSN-Protected amino acid 4-phenolsulfonic acid derivative esters, such as 2, 6-dibromo-4- sulfophenyl ester sodium salt, 2, 6-dichloro-4-sulfophenyl ester potassium salt and 2-nitro-4- sulfophenyl ester sodium salt, were prepared. These esters are water-soluble active esters, and were applied for the synthesis of Leu-enkephalin.View full abstractDownload PDF (828K) -
TAKUZO HISANO, KAZUNOBU HARANO, TOSHEKAZU MATSUOKA, HIROTOSHI YAMADA, ...1987 Volume 35 Issue 3 Pages 1049-1057
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSPericyclic reactions of 3, 5-lutidine N-oxide with N-phenylmaleimides were investigated. The primary cycloadducts are thermally labile and undergo 1, 5-sigmatropic rearrangement to give the 2, 3-dihydropyridine derivatives. The proton nuclear magnetic resonance structural assignment of the 1, 5-sigmatropy products implies that the primary cycloaddition proceeds through an exo transition state. The reaction behavior is discussed in terms of frontier molecular orbital theory, based on MINDO/3 and CNDO/2 calculations and kinetic data. It was concluded that the reaction falls into the category of a 'normal-type' cycloaddition and the exo cycloaddition is brought about by the unfavorable secondary orbital interaction.View full abstractDownload PDF (1219K) -
SHUNSAKU OHTA, SATOSHI HAYAKAWA, KAZUKO NISHIMURA, MASAO OKAMOTO1987 Volume 35 Issue 3 Pages 1058-1069
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS(1-Methyl-1H-imidazol-2-yl) methanol derivatives (4 and 7) were prepared by treating carbonyl compounds with 2-lithio-1-methyl-1H-imidazole (2) or by treating 2-acyl-1H-imidazoles (3) with organometallic reagents or sodium borohydride. The alcohols (4 and 7) were convertible into the carbonyl compounds via the corresponding quaternary salts (8 and 10). The stable (1-methyl-1 H-imidazol-2-yl) methanol system, R-C (OH) -C=N-CH=CH-NCH3, can be regarded as a masked form of the carbonyl group as well as a synthon of the group.View full abstractDownload PDF (1939K) -
MASARU KIHARA, TOMOMI KOIKE, YASUHIRO IMAKURA, KIYOSHI KIDA, TETSURO S ...1987 Volume 35 Issue 3 Pages 1070-1075
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTwo new alkaloids, demethylmaritidine (4) and (-) -N-demethyllycoramine (5), were isolated from the bulbs of Hymenocallis rotata HERB. (Amaryllidaceae) together with eleven known bases, vittatine (6), alkaloid-13 (7), 3-epimacronine (8), ismine (9), pretazettine (10), lycoramine (11), lycorine (12), tazettine (13), haemanthamine (14), galanthamine (15), and N-demethylgalanthamine (16).View full abstractDownload PDF (1033K) -
NOBUTAKA FUJII, OSAMU IKEMURA, SUSUMU FUNAKOSHI, HISAYUKI MATSUO, TOMI ...1987 Volume 35 Issue 3 Pages 1076-1084
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe usefulness of a new deprotecting procedure was demonstrated in the solution syntheses of two porcine spinal cord peptides, designated neuromedin U-8 and neuromedin U-25. Protected neuromedin U-8 (8-residue peptide), prepared by condensation of two fragments, served as a C-terminal amino component for the synthesis of neuromedin U-25 (25-residue peptide). Onto this fragment, five peptide fragments were successively condensed by the azide procedure to construct the entire amino acid sequence of neuromedin U-25, a possible biosynthetic precursor of neuromedin U-8. All protecting groups were cleaved from protected neuromedin U-8 and neuromedin U-25 by 1 M trimethylsilyl trifluoromethanesulfonate-thioanisole in trifluoroacetic acid. The results were compared with those obtained by trifluoromethanesulfonic acid deprotection. In terms of contractile activity in rat uterus, neuromedin U-25 was twice as active as neuromedin U-8.View full abstractDownload PDF (1569K) -
YUKARI SUZUKI, AKIRA MATSUDA, TOHRU UEDA1987 Volume 35 Issue 3 Pages 1085-1092
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS6, 5'-Cyclo -2', 5'-dideoxyuridine and 6, 5'-cyclo-5'-deoxythymidine, pyrimidine deoxynucleosides fixed in the anti conformation, were synthesized. The key intermediate, 3'-O-acetyl-5-chloro-2', 5'-dideoxy-5'-iodouridine (12), prepared from 2'-deoxyuridine, was cyclized by treatment with tributyltin hydride to the 6, 5'-cyclo derivative (13), then dehydrochlorinated to furnish, after de-O-acetylation, 6, 5'-cyclo-2', 5'-dideoxyuridine (14). For the synthesis of 6, 5'-cyclothymidine, 3'-O- acetyl -2', 5'-dideoxy-5'-iodo-5- phenylthiomethyluridine (22) was prepared from 2'-deoxyuridine and this compound was cyclized by treatment with tributyltin hydride to yield, after de-O-acetylaion, 6, 5'-cyclo-5'-deoxythymidine (24).View full abstractDownload PDF (1394K) -
NGUYEN HUY DUNG, BERNARD VIOSSAT, MICHEL CUGNON DE SÉVRICOURT, ...1987 Volume 35 Issue 3 Pages 1093-1097
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe crystal and molecular structure of 1, 4-bis- (cyclopropylmethyl) piperazine dihydrochloride has been determined by single-crystal X-ray diffraction analysis. The crystals are monoclinic, space group P21/c, with a=11.641 (7), b=7.017 (2), c=9.32 (4) Å, β=107.99 (6) °, Z=2. The structure was solved by direct methods. The hydrogen atoms were included in the refinement. The final R value is 0.035 for 1513 reflections considered to be observed. The bond distances and angles are in good agreement with the expected values. The 1, 4-bis- cyclopropylmethylpiperazinium (2+) ion has the “chair” conformation with a symmetry center. The crystal packing is due to the electrostatic attraction between chloride and nitrogen atoms, reinforced by hydrogen bonds.View full abstractDownload PDF (679K) -
MASAHARU TAMAI, CHIHIRO YOKOO, MITSUO MURATA, KIYOSHI OGUMA, KAORU SOT ...1987 Volume 35 Issue 3 Pages 1098-1104
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSEthly (+)-(2S, 3S) -3- [(S) -3-methyl-1- (3-methylbutylcarbamoyl) butylcarbamoyl] -2- oxirane-carboxylate (EST ; la) is expected to be useful as an oral therapeutic agent for muscular dystrophy on the basis of its potent inhibitory activities against the cysteine proteinases involved in the myofibrillar protein degradation that occurs in the disease. Through extensive investigations aimed at developing a new synthetic method for la that would be suitable for industrial application, it has been found that L-arginine can be used as a new, efficient resolving agent to obtain optically pure L-trans-epoxysuccinic acid (3a), and the active ester method using p-nitrophenol is very effective in the coupling reaction of ethyl L-trans-epoxysuccinate (7a) and L-leucine isoamylamide (8a) because of the extremely low formation of by-products.
To examine the contribution of the stereochemistry of the trans-epoxysuccinic acid and leucine moieties to the inhibitory activity against cysteine proteinases, the diastereomers (lb-d) of la were synthesized by a similar method and the rate constants of inactivation of papain by la-d were measured. Compound la, having L-trans-epoxysuccinic acid and L-leucine moieties, showed the most potent activity among them.View full abstractDownload PDF (1102K) -
GEN-ICHIRO NONAKA, YUKO GOTO, JUN-EI KINJO, TOSHIHIRO NOHARA, ITSUO NI ...1987 Volume 35 Issue 3 Pages 1105-1108
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFrom the leaves of Thujopsis dolabrata SIEB. et Zucc. (Cupressaceae), four new flavanonol glycosides, the 3-O-β-D-xylopyranosides (1→4) of (+) -taxifolin, (-) -taxifolin, (+) -epitaxifolin and (-) -epitaxifolin, together with (+) -catechin (5), (-) -epicatechin (6) and thirteen oligomeric procyanidins (7-19), were isolated and their chemical structures were characterized by spectroscopic and chemical investigations.View full abstractDownload PDF (682K) -
TOSHIO MIYASE, AKIRA UENO, NOBUO TAKIZAWA, HIROMI KOBAYASHI, HIROKO KA ...1987 Volume 35 Issue 3 Pages 1109-1117
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA new phenolic glycoside, icariside A1 (IV), and six new terpenic glycosides, icariside B1 (V), B2 (VI), C1 (VII), C2 (VIII), C3 (IX), and C4 (X), have been isolated from Epimedium grandiflorum MORR. var. thunbergianum (MIQ.) NAKAI, together with three known glycosides, salidroside (I), thalictoside (II) and benzyl glucoside (III). The structures of IV-X were established on the basis of chemical evidence and spectral data.View full abstractDownload PDF (1425K) -
HIROSHI TOKUNAGA, MASAYUKI TANNO, TOSHIO KIMURA1987 Volume 35 Issue 3 Pages 1118-1127
Published: March 25, 1987
Released on J-STAGE: February 12, 2010
JOURNAL FREE ACCESSThe mechanism of the color reaction and the structures of the colored products of cortisone (1a) and deoxycorticosterone (2a) with pyrrole were elucidated. In the presence of cupric acetate, la and 2a were converted to the oxidation products (1b and 2b) which have a glyoxal side chain at C (17). For studying the chemical structures of the colored products derived from corticoids, phenylglyoxal (3a) was used as a model compound with a glyoxal side chain. By reacting 3a with pyrrole in hydrochloric acid, di (2-pyrrolyl) benzoylmethane (3b) was produced as an intermediate in the formation of the colored product. Compound 3b was changed to [5- (2-pyrrolyl) -2 (2H) - pyrrolylidene] (2-pyrrolyl) benzoylmethane (3d) by reaction with pyrrole in the presence of cupric acetate and hydrochloric acid. Compound 3d in dichloromethane gave the absorption maximum at 480 nm. Corticoids 1b and 2b were converted to the colored products, 21- [5- (2-pyrrolyl) -2 (2H) - pyrrolylidene] -21- (2-pyrrolyl) -4-pregnene-3, 11, 20-trione (1e) and 21- [5- (2-pyrrolyl) -2 (2H) -pyrrolylidene] -21- (2-pyrrolyl) -4-pregnene-3, 20-dione (2e), by reaction with pyrrole under the above conditions. Corticoids 1e and 2e in dichloromethane gave absorption maxima at 510 and 480 nm, respectively. Corticoid 1e showed fluorescence at 562 nm with excitation at 516 nm.View full abstractDownload PDF (1265K) -
SUSUMU IWASA, EIKO KONISHI, KOICHI KONDO, TOHRU SUZUKI, HIDEYUKI AKAZA ...1987 Volume 35 Issue 3 Pages 1128-1137
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSAntitumor agents including mitomycin C (MMC) and methotrexate (MTX) were coupled to monoclonal antibodies against murine bladder tumor cell line MBT-2 for the purpose of enhancing their drug activity. MMC was conjugated with antibody through two carriers, periodate-oxidized dextran and dithiopyridylated serum albumin, and MTX was conjugated with antibody either directly or through dithiopyridylated serum albumin or poly-L-lysine via an amide bond. These conjugates were assayed for growth inhibitory effect on MBT-2 bladder tumor cells, MCA clone 15 embryo cells and P388 leukemic cells. The cytotoxicity tests demonstrated that drug-antibody immune conjugates were 10 to 100 times more cytotoxic against antibody-reactive MBT-2 cells than nonimmune drug conjugates and showed a similar level of cytotoxicity against antibody-nonreactive cells to that of the nonimmune conjugates. This selective cytotoxicity was also confirmed by competitive inhibition of unconjugated antibody, showing a dependency on antibody binding to the target cell surface antigens. The targeting effect was further assessed by evaluating the suppression of tumor growth subsequent to in vitro treatment of MBT-2 cells with immune conjugates. Half of the mice receiving cells treated with immune conjugates survived more than 40 d after inoculation, while none or one of 7 mice receiving cells treated with unconjugated drug, antibody alone or nonimmune conjugates survived at 40 d after inoculation.View full abstractDownload PDF (1794K) -
YOSHIO OKAWA, YUTAKA OZEKI, KO SUZUKI, KAZUHIKO SAKAI, SHIGEO SUZUKI, ...1987 Volume 35 Issue 3 Pages 1138-1143
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSPeritoneal exudate cells (PEC) from C3H/He mice given bakers' yeast mannans, WNM and WAM025, showed marked cytolytic activity against MM46 tumor cells in vitro. Because the cytotoxicity of the PEC was strongly inhibited by actinomycin D, it was assumed that the cytolytic factor was a proteinous material (s). Of the macrophages and polymorphonuclear leucocytes (PMN) separated from the PEC, only the former cells were found to display cytolytic activity. Quinacrine, a phospholipase A2, inhibitor, and sodium azide, a myeloperoxidase inhibitor, did not reduce the cytotoxicity of macrophages from mice treated with acidic mannan (WAM025). In contrast, diisopropylfluorophosphate, a serine protease inhibitor, inhibited the cytolysis of the MM46 target cells by WAM025-treated macrophages. Chymostatin, a chymotrypsin inhibitor, and elastatinal, an elastase inhibitor, also inhibited the cytolytic effect. It is therefore concluded that serine proteases secreted into the medium from the macrophages activated by mannans participated in the cytolytic destruction of neoplasmic cells.View full abstractDownload PDF (1069K) -
TSUTOMU MIMURA, SUSUMU ITOH, KAZUTAKE TSUJIKAWA, HIROSHI NAKAJIMA, MIK ...1987 Volume 35 Issue 3 Pages 1144-1150
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSLow-molecular-weight melanoprotein obtained from Ommastrephes bartrami LESUEL (Fr. SM II) was subjected to an anti-inflammatory screening procedure and was shown to have a potent inhibitory activity against carrageenin-induced rat paw edema. Fr. SM II was then studied with various acute inflammatory models and appeared to suppress the enhanced capillary permeability of mouse ear induced by xylene and the acceleration of vascular permeability induced by compound 48/80. Using the carboxymethylcellulose pouch method, both leucocyte emigration and protein exudation into the pouch fluid were potently inhibited by Fr. SM II. Fr. SM II was also effective in subacute inflammation induced by the felt pellet and the croton oil granuloma pouch methods. Thus, in addition to its anti-ulcerogenic activity, Fr. SM II also has anti-inflammatory activity.View full abstractDownload PDF (1097K) -
SHINICHI KOBAYASHI, FUSAYO YAMADA, MASANORI SASAKI, KIKUO ASAHINA, MAM ...1987 Volume 35 Issue 3 Pages 1151-1156
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSInteractions in vitro and in vivo between semi-alkaline proteinase (SAP) and protease inhibitors of rabbit serum were studied. As a result of the purification of SAP inhibitors from rabbit serum, the caseinolytic activity of SAP was found to be inhibited by α1-macroglobulin (α1 M) and α1proteinase inhibitor (α1, PI). SAP was stoichiometrically bound to α1M at a molar ratio of 1 : 1 and the proteolytic activity remained constant at 16% of the original activity even in the presence of excess α1 M. In contrast, the proteolytic activity of SAP decreased linearly with increase in the amount of α1 PI, but a 10-fold molar excess of α1PI was needed for complete inhibition.
The disappearance rate of intravenously injected 125I-labeled SAP (125I-SAP) from rabbit serum was also investigated by using high-performance liquid chromatography (HPLC). Serum levels of 125I-SAP decreased biexponentially after a single injection. The results of gel-permeation HPLC of rabbit serum on a TSK G-3000 SW column indicated that SAP was mainly bound to α-macroglobulins and that α-macroglobulin-SAP complex was cleared from the blood circulation with a half-life of 10 min.View full abstractDownload PDF (877K) -
TAKAKO YOKOZAWA, HAE YOUNG CHUNG, HIKOKICHI OURA1987 Volume 35 Issue 3 Pages 1157-1161
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe chronic effect of oral administration of Salviae Miltiorrhizae Radix extract on renal tissue blood flow and blood pressure was investigated in uremic rats. Chronic administration of the aqueous extract from Salviae Miltiorrhizae Radix to rats significantly increased renal tissue blood flow by 32 and 38% on days 12 and 24, respectively. Blood pressure measured by the tail-cuff method was significantly decreased by 4-8% on the 6th, 18th, and 24th d. The uremia-alleviating action of Salviae Miltiorrhizae Radix extract is discussed on the basis of the present results.View full abstractDownload PDF (739K) -
HIROAKI NANBA, ATSUKO HAMAGUCHI, HISATORA KURODA1987 Volume 35 Issue 3 Pages 1162-1168
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA polysaccharide was extracted from fruit bodies of Grifola frondosa (maitake), and the chemical structure and antitumor activity were studied. The extracted polysaccharide could be hydrolyzed by ?A-glucanase into glucose, indicating it to be a β-glucan. The sample gave methyl 2, 3, 4, 6- tetra-Ο-, methyl 2, 4, 646-Ο-, methyl 2, 3, 4-tri -Ο- and methyl 2, 4-di-Ο-methylglucoside in the molar ratio of 4 : 2 : 1 : 4 on methylation. In the carbon-13 nuclear magnetic resonance spectrum, the signals of C-6' (related to (1-6) bonding) and C-3' (related to (1-3) bonding) were observed in addition to those of free C-6 and C-3. These results indicate that the major chain is made up of β-1, 6-linked glucose residues with branches of β-1, 3-linked glucose. This glucan inhibited the growth of Sarcoma 180 tumor in ICR mice.View full abstractDownload PDF (900K) -
KIYOSHI KONISHI, HIROKAZU ADACHI, KIYOSHI KITA, ISAMU HORIKOSHI1987 Volume 35 Issue 3 Pages 1169-1175
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTannic acid inhibited the growth of Photobacterium phosphoreum in liquid culture and also decreased the viability, expressed in terms of the colony forming activity.
The activity of glucose dependent oxygen consumption of whole cells was inhibited by tannic acid. It was found that the activity of reduced nicotinamide adenine dinucleotide (NADH) oxidase of the sonicated membrane of Photobacterium phosphoreum decreased when tannic acid was added to the assay system. The results suggested that the targets of tannic acid action were NADH dehydrogenase and the terminal oxidase.
The inhibitory effect of tannic acid on the terminal oxidase was compared in the cases of purified terminal oxidase (cytochrome b560-d complex) and sonicated membrane vesicles. The oxidase activities toward ubiquinol-1 and N, N, N', N'-tetramethyl-p-phenylenediamine dihydrochloride (TMPD) in the presence of ascorbate were both inhibited by tannic acid in both sonicated membrane and purified cytochrome b560-d complex. The inhibition of ubiquinol-1 oxidase activity in sonicated membrane was biphasic and noncompetitive in both phases. The inhibition of the ubiquinol-1 oxidase activity of purified terminal oxidase was monophasic and noncompetitive. On the other hand, the inhibition of TMPD oxidase activity in the presence of ascorbate in both membrane vesicles and purified enzyme was uncompetitive. Thus, the mechanisms of inhibition of the two kinds of oxidase activity by tannic acid were different.View full abstractDownload PDF (1053K) -
HIROKAZU ADACHI, KIYOSHI KONISHI, KAZUO TORIIZUKA, ISAMU HORIKOSHI1987 Volume 35 Issue 3 Pages 1176-1182
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe in vitro effects of tannic acid on the membrane structure and function of rat liver mitochondria were investigated. The respiratory control ratio (RCR) decreased by about 50% on addition of 50 μg/ml tannic acid to highly coupled mitochondria, but the adenosine -5'- diphosphate/oxygen (ADP/O) ratio was constant. The uncoupler-induced respiration was also inhibited in the same manner as the RCR. Moreover, the respiratory control disappeared and the ADP/O ratio could not be measured at concentrations of tannic acid above 100 μg/ml. On the other hand, the oxygen consumption rate of succinate-dependent respiration decreased on addition of more than 100 μg/ml tannic acid (50% inhibitory concentration (IC50) = 150 μg/ml tannic acid) to mitochondria. These findings suggest that tannic acid at lower concentrations inhibits the electron transport system to decrease the RCR, but does not impair the membrane, retaining the coupled reaction, while at higher concentrations it impairs the structural integrity of mitochondrial membranes, and directly inhibits the electron transport system.
Tannic acid inhibited the succinate oxidase, reduced nicotinamide adenine dinucleotide (NADH) oxidase, succinate dehydrogenase, and NADH dehydrogenase activities of submitochondrial particles (SMP). The IC50 values of tannic acid toward these enzyme systems were estimated to be 35, 45, 30, and 15 μg/ml, respectively. Tannic acid competitively inhibited succinate dehydrogenase and NADH dehydrogenase. However, it did not show significant inhibition of the cytochrome oxidase activity of SMP. It is thus concluded that tannic acid exerts its effect on mitochondrial respiration and oxidative phosphorylation through action on the membrane and on both succinate dehydrogenase and NADH dehydrogenase of mitochondria.View full abstractDownload PDF (1022K) -
HIRAKU ONISHI, TSUNEJI NAGAI1987 Volume 35 Issue 3 Pages 1183-1188
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe previously reported method for the preparation of decylenediamine-dextran T70 (T70- C10) was improved, and several chemical properties of the polymer support were examined. Methotrexate (MTX) was conjugated to T70-C10 by using 1-ethyl-3- (3-dimethylaminopropyl) - carbodiimide hydrochloride. The T70-C10MTX conjugate (T70-C10MTX) and T70-C10 carrying adsorbed MTX (T70-C10·adsorbed MTX) were dialyzed in order to examine the nature of the adsorption of MTX on T70-C10MTX. Before and after dialysis, the activity of these derivatives was assayed in terms of the binding affinity to dihydrofolate reductase. A more stable T70-C10 was obtained by using more severe reaction conditions in the Schiff's base formation between diaminodecane (C10) and oxidized dextran T70 and in the subsequent reduction. Conjugation was successful and the separation by gel-filtration (Sephadex G50) was good. The chemical properties of T70-C10 and T70-C10MTX were consistent and similar to those of the previous preparations. From the dialysis experiment, T70-C10MTX was estimated to have about 5 to 6% of the inhibitory activity of free MTX.View full abstractDownload PDF (855K) -
HIROSHI KIWADA, TAKAAKI MIYAJIMA, YUREKO KATO1987 Volume 35 Issue 3 Pages 1189-1195
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSParticipating factors in the uptake of liposomes by the liver were examined in a small-volume circulating perfusion system. The volume of the perfusate was 23 ml, which corresponds to the blood volume of the rat. It is considered that this system is suitable for examining the factors participating in the uptake in vivo. An indispensable factor for the uptake was found in fresh serum, and the uptake proportionally depended on the amount of the factor in serum. The properties of the factor were investigated with serum pretreated in various ways. The experiment with preheated serum indicated that the factor is very heat-sensitive and may be a protein. When serum was dialyzed with a cellulose membrane, the activity penetrated through the membrane, and its molecular weight was concluded to be below 17000 daltons. The sum of the activities on both sides of the membrane in equilibrium dialysis was almost equal to that in fresh serum. This strongly suggests that the factor does not participate cooperatively with other factors in the uptake. The uptake activity disappeared when serum was incubated with liposomes at 38 °C for 5 min in advance. The interaction of the factor with liposomes appears to be very fast and irreversible.
Correspondence of the uptake by the liver and elimination from the perfusate in the perfusion system to the in vivo behavior after i.v. injection was also examined. Correspondence of the uptake was observed, but the elimination kinetics from perfusate and blood were different. It is suggested that the uptake is dominated by the factor described here, but the elimination kinetics is partially affected by other factor (s).View full abstractDownload PDF (1079K) -
KIYOSHI YAMAOKA, YOSHITAKA YANO, OSAMU SAKURAI, HISASHI TANAKA1987 Volume 35 Issue 3 Pages 1196-1200
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe effect of probenecid on the disposition of cefpiramide was studied in rats. Cefpiramide (50 mg/kg) was injected into rats through a femoral vein. Probenecid (75 or 150 mg/kg) was administered simultaneously with cefpiramide. The plasma concentration of cefpiramide and the amount excreted into the bile were monitored with a high-performance liquid chromatograph (HPLC). Population pharmacokinetics with Akaike's information criterion (AIC) was applied to analyze the effect of probenecid on the disposition of cefpiramide. The result of the AIC method was compared with that of the χ2 test. It was concluded that probenecid exclusively inhibits the biliary excretion of cefpiramide. The presence of probenecid does not influence the volume of distribution of cefpiramide or the non-biliary elimination rate. The administration of 75 mg/kg of probenecid markedly suppresses the biliary excretion of cefpiramide. However, the effect of 150 mg/kg of probenecid on the elimination rate of cefpiramide is almost the same as that of 75 mg/kg.View full abstractDownload PDF (756K) -
TOSHIAKI NAKAJIMA, YASUJI TAKASHIMA, KIN-ICHI IIDA, HARUMI MITSUTA, MA ...1987 Volume 35 Issue 3 Pages 1201-1206
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSMicroencapsulation of indomethacin (IM) was carried out by a simple coacervation method using ethylcellulose. To control the release of IM, its surface was modified by dry-blending it with a carboxy-vinyl polymer (Hiviswako 104, HW) by pulverization in an automatic ceramic mortar before encapsulation. Suppositories containing intact IM and micro-encapsulated IM (IM-MC) were prepared by the fusion method. Dissolution and release testing of the IM-MC and of the suppositories were carried out by the methods of JP X and Muranishi et al., respectively. The dissolution rate of micro-encapsulated intact IM decreased as the content of the coacervationinducing agent, polyethylene (PE), was increased. The release rate profile of the suppositories containing these microcapsules did not show an apparent zero-order release, and the release rate was rapid without PE. When the PE content was 1% (w/v), the release rate was too slow and a large portion of IM remained in the IM-MC. On the other hand, suppositories containing micro-encapsulated HW-modified IM (HW/IM = 1/1) showed an apparent zero-order release profile and about 100% of the IM in the IM-MC was released.
These results showed that the surface modification of IM with HW before encapsulation is a good method to prepare sustained-release suppositories containing IM-MC.View full abstractDownload PDF (1138K) -
NORIAKI OHNISHI, TERUYOSHI YOKOYAMA, YOSHIFUMI KIYOHARA, YOSHIAKI KITA ...1987 Volume 35 Issue 3 Pages 1207-1213
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe kinetics of the solid-state isothermal transition of bromovalerylurea polymorphic forms (I, II and III) at high temperature were investigated by means of differential scanning calorimetry. Kinetic analysis according to the method of Hancock and Sharp indicated that the transition of form I to form II follows the one-dimensional diffusion mechanism. The activation energy for this transition calculated from the Arrhenius plots was 826.2 kJ/mol. On the other hand, it was found that the transition of form III to form I conforms with the mechanism of random nucleation and two-dimensional growth of nuclei (Avrami-Erofeev equation). This activation energy was estimated to be 185.2 kJ/mol. It was concluded that the mechanism and the value of activation energy were both different between the two kinds of isothermal transitions of bromovalerylurea polymorphic forms.View full abstractDownload PDF (4830K) -
KADZUYA TANIGUCHI, NORIKO YAMAZAWA, KADZUE ITAKURA, KATSUHIKO MORISAKI ...1987 Volume 35 Issue 3 Pages 1214-1222
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSLiposome preparations containing dexamethasone or its ester derivatives were formulated as eye drops. Steroids were efficiently incorporated into the liposomes; the incorporation ratio was not affected by the period of sonication or the addition of stearylamine or dicetylphosphate, but was decreased by the addition of cholesterol. The incorporation ratio appears to be governed by partition equilibrium between the lipid membrane and the aqueous phase. A theoretical interpretation of the findings was attempted by using partition theory. No release of dexamethasone palmitate from liposomes was detected, but a small portion of other steroids was rapidly released when the liposome preparation was diluted with a buffer solution. The amount of steroid released from the liposomes may also be governed by the partition equilibrium.View full abstractDownload PDF (1231K) -
TOSHINOBU AOYAMA, MASAYOSHI HORIOKA1987 Volume 35 Issue 3 Pages 1223-1227
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSParticulate matter in micronomicin, sisomicin and tobramycin injection solutions sealed in glass ampules was identified as barium sulfate crystals by using scanning electron microscopy and energy dispersing X-ray analysis. Barium sulfate crystals isolated from these solutions occurred as single or agglomerated crystals which were 0.5-2.0 μm long in maximum dimension. Barium sulfate crystal formation in usual ampules tended to increase with increasing temperature of sterilization, but that in surface-treated ampules did not increase during sterilization at high temperature.View full abstractDownload PDF (4457K) -
TOSHIHISA YOTSUYANAGI, HOTAKA HASHIMOTO, MOTOKAZU IWATA, KEN IKEDA1987 Volume 35 Issue 3 Pages 1228-1233
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSLiposome disintegration by either ultrasonic vibration or sodium cholate solubilization was investigated as a function of cholesterol (CH) content in the egg phosphatidylcholine (PC) liposome membrane. Turbidity changes were used as an indication of the membrane stability to these stresses. First-order disintegration constants (κufor ultrasonic stress and κsfor sodium cholate solubilization) were calculated to evaluate the membrane stability. A plot of κu against membrane CH content gave a sigmoidal curve on which inflection points occurred at about 15 mol% and 33 mol% CH. In contrast, the plot of κs against membrane CH content gave a biphasic curve with only one inflection point at about 17 mol% CH. These results can be explained in terms of the molecular packing model of phospholipids and CH proposed by Presti et al. (Biochemistry, 21, 3831 (1982)). Disintegration by ultrasonic stress was little affected by the accumulation of CH-rich domains up to 15 mol% CH, but disintegration by sodium cholate was abruptly suppressed in the same CH. content range. These results indicate that the mechanisms of disintegration of CH-rich domains and interfacial boundary phospholipid are entirely different between the two stresses.
In the liposome disintegration by sodium cholate, it was suggested that the penetration-saturation step of the surfactant molecule into the bilayer is rate-determining for pure PC liposomes, while the lamellar-micellar transition step is rate-determining for CH-rich liposomes.View full abstractDownload PDF (1004K) -
MINEO SHIMIZU, SYUNJI HORIE, MUNEHISA ARISAWA, TOSHIMITSU HAYASHI, SHO ...1987 Volume 35 Issue 3 Pages 1234-1237
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe EtOH extract of “Tapecué, ” Acanthospermum australe, was found to have a potent inhibitory activity towards rat lens aldose reductase (AR). From the active fraction of the extract, 5, 7, 4'-trihydroxy-3, 6-dimethoxyflavone was isolated. It was found to have higher activity (IC50 = 1 × 10-7 M) than quercitrin, which is a known inhibitor of AR (IC50 =1.8 × 10-6 M in our bioassay).View full abstractDownload PDF (622K) -
SHOZO TSUTSUI, SEIKI TANADA1987 Volume 35 Issue 3 Pages 1238-1242
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe adsorption behavior of gas mixtures composed of hydrogen sulfide and dimethyl sulfide in the pores of N-containing activated carbon (N-CAC) was investigated on the basis of adsorption isotherms of the pure components and binary gas mixtures. Hydrogen sulfide and dimethyl sulfide were mainly adsorbed into smaller micropores and into larger micropores, respectively. The adsorption capacity of N-CAC for hydrogen sulfide was increased by 25-35% as compared with that of raw activated carbon (R-AC). The adsorption capacity of N-CAC for dimethyl sulfide was decreased by 20% as compared with that of R-AC. The experimental adsorption isotherms of binary gas mixtures at 'different molar ratios agreed closely with the theoretical adsorption isotherms on N-CAC. However, the experimental adsorption isotherms of the binary gas mixtures did not agree with the theoretical adsorption isotherms on R-AC and the amounts adsorbed on R-AC were very much smaller than the theoretical ones. These results indicated that adsorption of each component on N-CAC did not interfere with that of the other component, and that hydrogen sulfide and dimethyl sulfide entered micropores of different sizes in N-CAC. It was concluded that N-CAC is a characteristic adsorbent having a greater adsorption capacity for hydrogen sulfide in these binary gas mixtures. It seemed that adsorption of the binary gas mixtures was mainly competitive on R-AC and selective on N-CAC.View full abstractDownload PDF (684K) -
SHOZO MIYAZAKI, TSUGUYA NAKAMURA, CHIZUKO YOKOUCHI, MASAHIKO TAKADA1987 Volume 35 Issue 3 Pages 1243-1248
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSIndomethacin gel preparations made by dissolving the drug in Pluronic aqueous gels were administered rectally to rabbits and the drug plasma levels were determined. When indomethacin gel preparations with 20% (w/w) Pluronic F-127 were given to rabbits, the plasma concentration reached the maximum level 0.5 h after administration. On the other hand, the 25% (w/w) Pluronic F-127 gel preparation did not show a sharp peak of plasma concentration and produced a sustained-release effect. The 30% (w/w) gel preparation also gave a sustained-release effect, but it was not a desirable preparation because its [AUC] 100 was only half that of a commercial suppository. Pluronic F-108 and Pluronic F-98 did not give a sustained-release effect at the concentration of 25% (w/w).
Damage to the mucosal membrane by Pluronic F-127 was rarely found in the rectum. In addition, the individual differences in drug plasma levels following rectal administration of the 25% (w/w) Pluropic F-127 gel preparation were small compared with those of other preparations.
These results suggest that the 25% (w/w) Pluronic F-127 gel is most suitable for use as a vehicle for rectal administration of indomethacin with prolonged action and with reduced side effects.View full abstractDownload PDF (1133K) -
KAZUHARU IENAGA, KUNIHIKO HIGASHIURA, HIROSHI KIMURA1987 Volume 35 Issue 3 Pages 1249-1254
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTwelve dipeptides (1-12) containing y-aminobutyric acid (GABA : H-γAbu-OH : 37) at the C-terminal were synthesized. Another six dipeptides (13-18) containing GABA analogues such as γ-amino-β-hydroxybutyric acid [GABOB : H-γAbu (2OH) -OH : 38], β-alanine (39) and ε-aminocapric acid (EACA : εAcp : 40) at the C-terminal were also synthesized. Their properties are presented, together with preliminary findings on the immuno-crossreactivity with antiserum against GABA.View full abstractDownload PDF (832K) -
KEIICHI ITO, JUNKO MARUYAMA1987 Volume 35 Issue 3 Pages 1255-1261
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA series of 4-diazomethyl-2 (1H) -quinolinones 4a-f was prepared, and the physical and chemical properties were compared with those of the known 4-diazomethylcoumarins. In view of their easy accessibility, high stability and reactivity, these new diazoalkanes are expected to be practical reagents for the fluorescence labeling of carboxylic acids, although the fluorescence intensities of the labeled esters are less than those of the esters with the corresponding coumarin reagents.View full abstractDownload PDF (695K) -
TOKUJIRO KITAGAWA, HIROKO KURODA, HIDEAKI SASAKI1987 Volume 35 Issue 3 Pages 1262-1265
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSAliphatic, aromatic, and heteroaromatic carboxylic acids (5a-i) react with 1, 1'-oxalyldiimidazole (6) in acetonitrile under reflux in the presence of methanesulfonic acid (12) to give the corresponding carboxylic acid anhydrides (9a-i) in 30-98% yields.View full abstractDownload PDF (364K) -
NOBUTAKA FUJII, YOSHIO HAYASHI, KENICHI AKAJI, SUSUMU FUNAKOSHI, MASAH ...1987 Volume 35 Issue 3 Pages 1266-1269
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA newly found rabbit stomach peptide, H-Pyr-Val-Asp-Pro-Asn-Ile-Gln-Ala-OH, was synthesized by the solid-phase method. A new polymer support, cross-linked polystyrene-polypropylene composite fiber (IONEX), was employed to facilitate multiple washing processes in chain elongation reactions. β-Cycloheptyl aspartate, Asp (OChp), was employed for the first time in this solid-phase peptide synthesis. In the final step of the synthesis, the peptide was cleaved from the resin, together with other protecting groups employed, by treatment with 1 M trimethylsilyl trifluoromethanesulfonate thioanisole in trifluoroacetic acid. The deprotected peptide was found to be identical with the sample obtained from the natural source.View full abstractDownload PDF (384K) -
KOICHI MORI, KYOKO TAKAHASHI, TAKEO KISHI, HIROTERU SAYO1987 Volume 35 Issue 3 Pages 1270-1274
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSNew 2, 3-dimethyl-1, 4-benzoquinones having an alkylthio or arylthio side chain at the 5-position and two alkylthio side chains at the 5-and 6-position were synthesized as possible antimetabolites of coenzyme Q. These compounds were tested for inhibition of coenzyme Q in mitochondrial succinoxidase and reduced nicotinamide adenine dinucleotide (NADH) -oxidase systems, and were found to show greater inhibition of the NADH-oxidase system than of the succinoxidase system. 5, 6-Di-octylthio-2, 3-dimethyl-1, 4-benzoquinone showed greater inhibitory activities than 5-alkylthio-2, 3-dimethyl-1, 4-benzoquinones. 5-Arylthio-2, 3-dimethyl-1, 4-benzoquinones showed potent inhibitory activities towards both enzyme systems.View full abstractDownload PDF (598K) -
HIDEAKI MATSUDA, REIKO MATSUDA, SEIYA FUKUDA, HIDEMI SHIOMOTO, MICHINO ...1987 Volume 35 Issue 3 Pages 1275-1280
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe anti-thrombic activities of a 70% methanolic extract (CMe) from Cinnamomi Cortex on blood coagulation and fibrinolysis were investigated. CMe prevented the hepatic venous thrombosis in high butter diet-treated rats, and the decreases of blood platelets and fibrinogen in normal rats induced by endotoxin. CMe also inhibited the blood platelet aggregation induced by collagen, arachidonic acid and adenosine diphosphate (ADP) and the conversion of fibrinogen to fibrin induced by thrombin in in vitro experiments. Cinnamic aldehyde, a major. essential oily component of CMe were showed stronger inhibitory activity than that of CMe on the blood coagulation. These results suggest that Cinnamomi Cortex has anti-thrombic activities.View full abstractDownload PDF (704K) -
RIKA NONOYAMA, TOSHIKO NAITO, MIYUKI TAKAYANAGI, SHOJI GOTO, TAMOTSU Y ...1987 Volume 35 Issue 3 Pages 1281-1284
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA spectrophotometric method for determination of salicylaldehyde (SA) with 1, 3-diphenyl-2-thiohydantoin (DPTH) is described. The method is based on the formation of a pigment having an absorption maximum at around 510 nm from SA in acetone in the presence of sodium hydroxide. This method is simple and allows the determination of SA in the concentration range of 0.2-10 μM/ml.View full abstractDownload PDF (414K) -
HIROAKI NANBA, HISATORA KURODA1987 Volume 35 Issue 3 Pages 1285-1288
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe chemical structure and antitumor activities of a polysaccharide from mycelia of Cochliobolus miyabeanus (Ascomycetes) were examined. The polysaccharide extracted with 4 N acetic acid was purified by Sepharose CL-4B and diethylaminoethyl (DEAE) -Sepharose column chromatography; 0.3 g of this antitumor glucan (As-I) was obtained from 100 g of dried mycelia. The purified polysaccharide (As-I) contains 99.1% sugar and 0.9% protein and its molecular weight was approximately 1.2 × 106. The chemical structure of As-I was determined by methylation, Smith degradation and carbon-13 nuclear magnetic resonance analyses. The results suggested that As-I has a 1, 3-linked main chain with branches from the 6 position of some glucose residues. As-I (0.5 mg/kg/d) caused tumor growth inhibition in the allogeneic system of ICR mice-Sarcoma 180 tumor (50% inhibition ratio) when given by intraperitoneal injection.View full abstractDownload PDF (428K) -
HIROAKI NANBA, HISATORA KURODA1987 Volume 35 Issue 3 Pages 1289-1293
Published: March 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe polysaccharide As-I, a β-1, 3 glucan possessing 1, 6-linked side chains, isolated from mycelia of Cochliobolus miyabeanus (Ascomycetes) , inhibited the growth of Sarcoma 180 solid tumor in ICR mice. As-I also inhibited the growth of solid tumors of IMC-carcinoma in CDF1 mice by 32% and that of solid tumors of MM-46 carcinoma in C3H mice by 99.3% at 0.1 mg/kg/d (10 times). However, As-I has no direct cytotoxic activity against tumor cells. The effect of As-I on macrophages was studied, because branched β-1, 3 glucans may stimulate cellular immunity. As-I activated macrophage spreading and phagocytosis of tumor cells. Accordingly, the antitumor activity of As-I might be host-mediated, like that of other β-1, 3 glucans.View full abstractDownload PDF (505K)