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Volume 36, Issue 8
Displaying 1-50 of 82 articles from this issue
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JUZIRO NISHIJO, EMIKO IWAMOTO, IKUKO YONETANI, SATSUKI TOKURA, MAKIKO ...1988 Volume 36 Issue 8 Pages 2735-2741
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of theophylline with L-tryptophan was investigated in aqueous solution adjusted to ionic strength 0.20, at pD 6.2, by using proton nuclear magnetic resonance spectroscopy. Theophylline interacted with L-tryptophan at a molar ratio of 1 : 1 by parallel stacking. The thermodynamic parameters obtained for the complexation were as follows : ΔG°=-1.52kcal/mol (K=13.1M-1), ΔH°=-5.1kcal/mol, ΔS°=-12.3 e.u. It was found that the driving force for parallel stacking is a combination of electrostatic, polarization, and dispersion interactions, and the contribution of hydrophobic bonding is small. A possible stacking mode is postulated, based on the complexation shifts and π-electron charge distributions of theophylline and L-tryptophan.View full abstractDownload PDF (636K) -
MASAYUKI NAKAGAKI, KAZUHIRO INOUE, HIROAKI KOMATSU, TETSUROU HANDA, KO ...1988 Volume 36 Issue 8 Pages 2742-2749
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of concentration of sodium dodecyl sulfate (SDS) on the efficiency of photooxidation of methyl orange (MO) sensitized with tetraphenylporphyrin (TPP) in SDS aqueous solution was investigated. Below the critical micelle concentration of SDS-TPP mixed solution (cmcmix), TPP was solubilized as an oligomer complex composed of one or plural TPP molecules and plural SDS ones; only the oligomer complex composed of one TPP molecule and plural SDS ones (TPPm-SDSs complex) among the oligomer complexes contributed to the efficient photooxidation of MO. Above the cmcmix, however, the reaction efficiency decreased with increase in the SDS concentration. Above the cmcmix, all the TPP molecules were not always solubilized without aggregating among themselves in the micellar phase and some of the TPP molecules were solubilized as TPPm-SDSs complexes in the aqueous phase. With increase in the SDS concentration, the TPPm-SDSs complexes were absorbed into the micelle and TPP monomer was increased in the micellar phase, where TPP had a lower reaction efficiency than TPP solubilized as a TPPm-SDSs complex due to the less polar environment in the micellar phase. Thus, above the cmcmix, the diminution of the reaction efficiency with increasing SDS concentration could be ascribed to the decrease in the amount of TPP monomer solubilized as a TPPm-SDSs complex.View full abstractDownload PDF (753K) -
TOMOYA SAKAI, MICHIO SUZUMURA, DAISUKE NOHARA1988 Volume 36 Issue 8 Pages 2750-2758
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Chymotryptic hydrolyses of globular proteins, α-chymotrypsin (Chym) and catalase (Cata), were examined kinetically at pH 7.8 and temperatures between 30 and 50°C. In both cases, the reactions followed second-order rate equations; -d[Chym]/dt=k(chy-chy)[Chym]2 for the autolysis of Chym and -d[Cata]/dt=k(chy-cat)[Chym] [Cata] for the chymotryptic hydrolysis of Cata. From the Arrhenius plots, ΔH≠/kJ mol-1 and ΔS≠/JK-1 mol-1 were obtained as follows : for k(chy-chy)/dm3 mol-1 s-1, 270 and 681 at 30-44°C, and for k(chy-cat)/dm3 mol-1 s-1, 72.0 and 2.32 at 30-42°C, respectively. At higher temperatures than 45°C, the Arrhenius plots showed upward-concave curvatures in both cases. These extremely large activation parameters obtained for Chym autolysis and moderately large activation parameters obtained for Cata proteolysis are discussed in terms of deformation of the three-dimensional structures and the sites of proteolysis in the globular structures of the two enzymes.View full abstractDownload PDF (740K) -
YUKO YOSHIKAWA, HIROSHI TERADA1988 Volume 36 Issue 8 Pages 2759-2765
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe ion-pair partition of methyl orange anion with the alkali metal cations Na+, K+ and Cs+ in an octanol-water system was studied at various temperatures. The ion-pair partition process could be divided into two processes; ion-pair formation and transfer of the ion-pair. The results showed that the degree of ion-pair formation increased with temperature, while the degree of partition of an ion-pair decreased with temperature for all alkali metal cations. The ion-pair partition of methyl orange anion was shown to be greatest with Cs+. The thermodynamic parameters ΔGθ, ΔSθ and ΔHθ for these two processes were determined. The values are discussed in relation to the degree of hydration of these alkali metal cations.View full abstractDownload PDF (660K) -
JACQUES DESBOEUFS, CHRISTIANE RALAMBOSOA, JACQUES ASTOIN, CLAUDE JORAM ...1988 Volume 36 Issue 8 Pages 2766-2771
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn insoluble polysaccharide with immunostimulating activity, which we have designated as pichilan, was isolated from the cell wall of Pichia fermentans (CBS 187) by repeated treatment with hot alkali and hot acetic acid. Partial hydrolysis led to the liberation of laminariosides and gentiobiose. A study of the products obtained by methylation, Smith degradation and endoglucanase hydrolysis showed that the polysaccharide is a moderately branched, (1→3)-β-D-glucan with a high molecular weight (approximately 200000) containing 10% β-(1→6)-linked glucopyranosyl residues and two different types of branches, a single glucosyl group and a long glucosyl chain.View full abstractDownload PDF (739K) -
TOSHIHIRO FUJIOKA, MASAYO IWAMOTO, YUKIKO IWASE, HIKARU OKABE, KUNIHID ...1988 Volume 36 Issue 8 Pages 2772-2777
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the dried herb of Actinostemma lobatum MAXIM. (Cucurbitaceae), two new baccharane-type triterpene glycosides, actinostemmosides E and F, were isolated. The structure of actinostemmoside F was elucidated mainly on the basis of 13C-13C-nuclear magnetic resonance (NMR) correlation spectrometry as the 3-O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside of 3β, 17β, 21, 26, 30-pentahydroxybacchar-24-ene. The structure of actinostemmoside E was determined as the 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside of 3β, 17β, 21, 26-tetrahydroxybacchar-24-ene by comparison of the 1H- and 13C-NMR spectra with those of actinostemmoside F.View full abstractDownload PDF (620K) -
NORIKO SHIMIZU, MASASHI TOMODA1988 Volume 36 Issue 8 Pages 2778-2783
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel minor polysaccharides, designated as MVS-IIA and MVS-IIG, were isolated from the seeds of Malva verticillata L. They were each homogeneous on electrophoresis and gel chromatography, and their molecular weights were estimated to be 57000 and 10400, respectively. MVS-IIA is composed of L-arabinose : D-galactose : D-mannose in the molar ratio of 14 : 28 : 1, and MVS-IIG is composed of D-glucose : D-galactose : D-manose in the molar ratio of 10 : 1 : 1. Methylation analysis, 13C-nuclear magnetic resonance, and Smith degradation studies enabled elucidation of their structural features.View full abstractDownload PDF (629K) -
FUMIKO ABE, RONG-FU CHEN, TATSUO YAMAUCHI1988 Volume 36 Issue 8 Pages 2784-2789
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix new iridoids, i.e., 13-O-caffeoylplumieride, 13-deoxyplumieride, β-dihydroplumericinic acid glucosylester, 1α-plumieride, 1α-protoplumericin A, and 8-isoplumieride, were isolated from the polar fraction of the methanol percolate of the roots of Plumeria acutifolia. The structures were determined by chemical and spectral methods.View full abstractDownload PDF (681K) -
RYOKO GONDA, MASASHI TOMODA, MIEKO KANARI, NAOMI YONEDA, TOWAKO SHIMIZ ...1988 Volume 36 Issue 8 Pages 2790-2795
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe major pectic peptidoglycan, designated as MVS-V, was isolated from the seeds of Malva verticillata L. It was homogeneous on electrophoresis and gel chromatography. It was composed of about 43% polysaccharide and 57% protein moieties, and its molecular weight was estimated to be 22000. The polysaccharide moiety was isolated, and found to be composed of L-arabinose : D-xylose : D-galactose : L-rhamnose : D-galacturonic acid in the molar ratio of 6 : 5 : 3 : 8 : 24. One-sixth of the D-galacturonic acid residues exist as the methyl esters. O-Acetyl groups were identified, and the content amounted to 3.3% of the polysaccharide moiety. Methylation analysis of the carboxyl-reduced derivative, nuclear magnetic resonance, periodate oxidation, and partial hydrolysis studies enabled elucidation of the structural features of the polysaccharide moiety. It is a pectic substance having a rhamnogalacturonan backbone with arabinoxylogalactan side chains. Several oligosaccharides belonging to the raffinose family were also isolated and identified from the seeds.View full abstractDownload PDF (733K) -
KAZUHARU IENAGA, KO NAKAMURA, KUNIHIKO HIGASHIURA, YOSHIO TOYOMAKI, HI ...1988 Volume 36 Issue 8 Pages 2796-2801
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlthough taurine-dipeptides containing an acidic α-amino acid (Glu or Asp) have been proposed to exist in the central nervous system, it is not yet clear how the acidic amino acid is linked with taurine in the peptides. This study aimed to analyze the mode of linkage of such peptides through analysis of their spectral data, such as proton nuclear magnetic resonance and mass spectra. Four pairs of taurine-oligopeptides (1-8) containing one acidic α-amino acid were examined, and spattered ion mass spectrometry B/E linked scan mass spectrometry was proved to be most useful to distinguish each pair of isomers. Further, immunochemical examination indiated that all the oligopeptides (1-8) synthesized by the conventional coupling method were highly cross-reactive with antisera against taurine and against γGlu-Tau.View full abstractDownload PDF (638K) -
JOSE M. AGUIRRE, ADRIANA F. IBANEZ, ELBA N. ALESSO, DORA G. TOMBARI, G ...1988 Volume 36 Issue 8 Pages 2802-2807
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral N-(monosubstituted ethyl)amides were synthesized and their carbon and proton nuclear magnetic resonance (13C and 1H-NMR) spectra were determined. Both (Z) and (E) stereoisomers could be observed in the formamides, but only the (Z) isomer was identified in the acetamides and phenylacetamides. The main body of the 1H-NMR results indicated that the methylene protons were equivalent. This finding is interpreted in terms of free rotation around the -CH2-CH-bond and magnetic equivalence. In cases where the 1H-NMR spectra revealed and ABX pattern, an interpretation is offered based on different populations among "pure staggered"conformers.View full abstractDownload PDF (590K) -
KAZUMI NAKAMURA, TAKETOSHI YAMADA, YOSHINORI FUJIMOTO, KATSUMI KAKINUM ...1988 Volume 36 Issue 8 Pages 2808-2812
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3β, 6α-Dihydroxycholesta-9(11), 17(20), 24-trien-23-one (2), the aglycone of acrosome reaction-inducing steroidal saponin Co-ARIS II (1), was synthesized from asterone diacetate (3) in 8 steps. The side chain was constructed by the coupling reaction of the allyl chloride (8) with the dithiane anion (9). Evidence for 17(20)-E stereochemistry of 2 was obtained by nuclear Overhauser effect (NOE) experiments in the proton nuclear magnetic resonance (1H-NMR) spectrum. Comparison of the 1H- and 13C-NMR data of 2 with those of 1 confirmed the structure assignment of the latter compound.View full abstractDownload PDF (583K) -
SANAE EGUCHI, SANAE YAMAGUCHI, MITSUKO FURUYA, MASUO MORISAKI1988 Volume 36 Issue 8 Pages 2813-2818
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a search for an alternative synthetic route to 32-oxygenated sterol derivatives such as 5, 7α, 8α- and 7β, 8β-epoxycholestanol acetate (9 and 10) were subjected to various conditions of epoxide cleavage. The trans-diaxial opening of the α-epoxide 9 with lithium/ethylamine gave the 7α-ol 11, whereas the 8β-ol 12 was produced from the β-epoxide 10 on reduction with lithium aluminum hydride. However, the trans-diaxial 8β-halo(or hydroxy)-7α-ols were not obtained at all on treatment of the α-epoxide 9 with various mineral acids or BF3-etherate in benzene. Under these conditions, the C-8 carbenium ion would be the intermediate, from which the 7-ketone 13 and a mixture of Δ6, 8-, Δ7, 9-, Δ7, 14- and/or Δ8, 14-diene compounds 16, as well as Δ-<8(9)>- and Δ8(14)-7α-ol 14 and 4a, were produced. The latter allylic alcohol 4a, a possible synthetic precursor of 32-oxygenated sterol was prepared in 63% yield when benzene was replaced with tetrahydrofuran in the BF3-etherate-catalyzed reaction of the α-epoxide 9.View full abstractDownload PDF (689K) -
ISAO KITAGAWA, TOSHIO TANIYAMA, YOSHIKO NAGAHAMA, KAZUYOSHI OKUBO, FUM ...1988 Volume 36 Issue 8 Pages 2819-2828
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy means of high performance liquid chromatography and other methods, three new partially acetylated soyasaponins, named acetyl-soyasaponin A1 (6a), acetyl-soyasaponin A2 (7a), and acetyl-soyasaponin A3 (8a), were isolated from American soybeans, the seeds of Glycine max MERRILL., together with hitherto known soyasaponins I (3), II (4), and III (5). Acetyl-soyasaponins A1, A2, and A3 are noteworthy due to their bitter and astringent tastes, although their parent saponins, soyasaponins A1 (6), A2 (7), and A3 (8), do not show such tastes.By virtue of the photochemical degradation method for the glucuronide linkage and on the basis of 1H- and 13C-nuclear magnetic resonance and secondary ion mass spectrum analyses, structures of acetyl-soyasaponins A1, A2, and A3 have been elucidated as 3-O-[β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (6a), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (7a), and 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopy-ranosyl]-22-O-[2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soya-sapogenol A (8a), respectively.View full abstractDownload PDF (960K) -
TOSHIO TANIYAMA, YOSHIKO NAGAHAMA, MASAYUKI YOSHIKAWA, ISAO KITAGAWA1988 Volume 36 Issue 8 Pages 2829-2839
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn addition to soyasaponins I, II, and III, three new bitter and astringent bisdesmosides named acetyl-soyasaponin A4(2), acetyl-soyasaponin A5 (3), and acetyl-soyasaponin A6 (4) which are characterized by having a fully acetylated terminal xylosyl moiety, have been isolated from a Japanese species of soybean (Tamanishiki strain), the seeds of Glycine max MERRILL, cultivated in Hokkaido Prefecture. By means of photochemical degradation (a selective cleavage method for the glucuronide linkage), and on the basis of physicochemical evidence including 1H- and 13C-nuclear magnetic resonance analysis, the structures of acetyl-soyasaponins A4, A5, and A6 have been elucidated as 3-O-[β-D-glucopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2, 3, 4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (2), 3-O-[β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2, 3, 4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (3), and 3-O-[α-L-arabinopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[2, 3, 4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (4), respectively.View full abstractDownload PDF (1231K) -
KENICHIRO MORI, KAZUO IGUCHI, NOBUKO YAMADA, YASUJI YAMADA, YOSHINOBU ...1988 Volume 36 Issue 8 Pages 2840-2852
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new bioactive marine diterpenoids, stolonidiol (1), stolonidiol monoacetae (2), and claenone (3), were isolated from Japanese soft coral of the genus Clavularia. The structures of these diterpenoids were elucidated on the basis of spectroscopic data including two-dimensional nuclear magnetic resonance, chemical reactions, and/or X-ray crystallographic analysis. Compounds 1 and 2 showed a strong cytotoxic activity against P388 leukemia cells, and 3 was inhibitory in the fertilized sea urchin egg assay.View full abstractDownload PDF (1063K) -
HARUKO TAKECHI, MINORU MACHIDA, YUICHI KANAOKA1988 Volume 36 Issue 8 Pages 2853-2863
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUpon irradiation in acetone, N-(ω-indol-3-ylalkyl)phthalimides (1, n=2-5) underwent intramolecular Paterno-Buchi reaction to give oxeto[2, 3-b]indoles or their ring-opening products. However, N-(ω-indol-2-ylalkyl)phthalimides (9, n=2, 3) yielded not the oxetane, but the N-deacetylated compounds.View full abstractDownload PDF (1085K) -
CHUZO IWATA, MINORU YAMADA, YASUO IDA, TOMOKO IMAO, HIROKO MIYAGAWA, K ...1988 Volume 36 Issue 8 Pages 2864-2871
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with our synthetic work on spirocyclic sesqui- and diterpenes, neighboring hydroxyl group participation in metal-ammonia reduction of hydroxyspirodienones was studied. The role of the hydroxyl group in the regioselective metal-ammonia reduction was clearly established.View full abstractDownload PDF (842K) -
CHUZO IWATA, TOMOHIRO AKIYAMA, KAZUYUKI MIYASHITA1988 Volume 36 Issue 8 Pages 2872-2877
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first total synthesis of (5R*, 6R*)- and (5R*, 6S*)-9-(bromomethylene)-1, 2, 5-trimethyl-spiro[5.5]undeca-1, 7-dien-3-one (1a and 1b) was achieved stereoselectively. The relative configuration of C-5 and C-6 of the natural product Z-1 was elucidated as 5R* and 6R* by comparison with our synthetic samples.View full abstractDownload PDF (758K) -
CHUZO IWATA, TOMOHIRO AKIYAMA, KAZUYUKI MIYASHITA1988 Volume 36 Issue 8 Pages 2878-2886
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-(2R*, 5aS*, 7R*, 8R*, 9aR*)- and (2R*, 5aS*, 7S*, 8S*, 9aR*)-7-Bromo-8-chloro-decahydro-2, 5a-methano-1-benzoxepin (1 and 2), the 11, 11-dedimethyl-7-demethylene derivative of nidifocene and its isomer, were stereoselectively synthesized via the bromohydrin 3 and 4 starting from the exo-diene 14.View full abstractDownload PDF (890K) -
JYOJI KURITA, HIROICHI SAKAI, TAKASHI TSUCHIYA1988 Volume 36 Issue 8 Pages 2887-2896
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of the 8-oxa-3, 4-diazatricyclo[5.1.0.0.2, 6]oct-4-enes (17) prepared from the 1, 2-diazepines (9) via five steps resulted in a ring transformation to give the 2, 3-diazabicyclo[3.1.0]hex-3-enes (20), whereas the 8-aza analogues (18) gave the 2-amino-3-cyano-5-azabicyclo[2.1.0]pentanes (23) by cleavage of the N-N bond. On the other hand, flash vacuum pyrolysis of the 8-oxa compounds 17 resulted in rearrangement to give the 1-amino-2-formylpyrroles (27), presumably via the expected 1, 4, 5-oxadiazocines (29), whereas the 8-aza compounds 18 gave the 3a, 6a-dihydro-pyrrolo[2, 3-c]pyrazoles (33) through a different type of rearrangement.View full abstractDownload PDF (1082K) -
TADASHI EGUCHI, YOSHINORI FUJIMOTO, KATSUMI KAKINUMA, NOBUO IKEKAWA, M ...1988 Volume 36 Issue 8 Pages 2897-2901
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new withanolide having a hydroxyl group at the C-23 position has been isolated from the leaves of Physalis peruviana. The structure of this withanolide has been established to be (20S, 22R, 23R)-6α-chloro-4β, 5β, 14α, 17β, 20, 23-hexahydroxy-1-oxowitha-2, 24-dienolide (1) by spectroscopic evidence.View full abstractDownload PDF (482K) -
TAISEI UEDA, YUZO KATO, JINSAKU SAKAKIBARA, MITSUO MURATA1988 Volume 36 Issue 8 Pages 2902-2908
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel classes of heterocycles, isoselenazolo[4, 3-e][1, 4]diazepines (3a-c, g, h, k, l, m) and isothiazolo[4, 3-e][1, 4]diazepines (3d-f, i, j, o) were synthesized from 7-oxo-6-phenyl-6H-isoselenazolo (or -isothiazolo)[4, 3-d]pyrimidines (1a, b) and 4, 6-dimethyl 5, 7-dioxo-4, 5, 6, 7-tetrahydro-isoselenazolo (or isothiazolo)[4, 3-d]pyrimidines (2a, b).View full abstractDownload PDF (691K) -
CHUZO IWATA, KOHJI HATTORI, TOSHIO KUROKI, SHUJI UCHIDA, TAKESHI IMANI ...1988 Volume 36 Issue 8 Pages 2909-2917
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereoselective and novel method for construction of the spiroketal moiety is described, as illustrated by a synthesis of (2R*, 5R*)- and (2R*, 5S*)-2-methyl-1, 6-dioxaspiro[4.5]decane (2A and 2B).The sulfide (7), prepared from a lactone (4), was oxidized with sodium metaperiodate followed by treatment with an acid to provide the two sulfoxide products (3A and 3B) in a 1 : 1 ratio. Acid-catalyzed cyclization of both compounds gave the corresponding dioxaspiro derivatives (9 and 10) without significant stereoselectivity, while their intramolecular bromohydrin formation reactions exhibited moderate stereoselection. Upon treatment with N-bromosuccinimide (NBS) followed by reductive operations, 3A gave 9a and 3B afforded 10d as major products. On the other hand, base-catalyzed intramolecular Michael reactions of 3A and 3B yielded 9b and 10c with extremely high stereoselectivity. These two dioxaspiro products were found to isomerize to the corresponding more stable isomers 9d and 10a on acidic treatment. Desulfurization of 9b or 10a afforded 2A and that of 9d or 10c gave 2B without any isomerization at the spiro center.View full abstractDownload PDF (871K) -
NAOYUKI ISHII, AKIRA TAKAHASHI, GENJIRO KUSANO, SHIGEO NOZOE1988 Volume 36 Issue 8 Pages 2918-2924
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the lipophilic fraction of fresh Polyporus dispansus, three new farnesylphenols (III, IV, V) and a new isopentenyphenol (VII)were isolated along with grifolin (II), O-methylgrifolin (I) and grifolic acid (VI). The structures of these new compounds were elucidated as shown in formulas III, IV, V and VII, respectively, on the basis of spectral and chemical evidence. Grifolin (II) and neogrifolin (VIII) were also isolated from P. confluens.View full abstractDownload PDF (734K) -
TSUTOMU HATANO, TAKASHI YOSHIDA, TETSURO SHINGU, TAKUO OKUDA1988 Volume 36 Issue 8 Pages 2925-2933
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe glucose carbon signals in the 13C nuclear magnetic resonance (NMR) spectra of hydrolyzable tannins forming anomer mixtures, which differ from each other in the locations of acyl groups, were assigned. The utility of these data was demonstrated by application to the structural assignments of recently isolated dimeric hydrolyzable tannins [e.g., camptothin A (13) and camptothin B (14)].View full abstractDownload PDF (635K) -
SHINZO KANO, YOKO YUASA, TSUTOMU YOKOMATSU, KENJI ASAMI, SHIROSHI SHIB ...1988 Volume 36 Issue 8 Pages 2934-2939
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS8a-Aryloxazolo[3, 4-a]cyclopenta[d]pyridines (9a-c) were prepared via a route involving radical cyclization of α-acylamino radical-polyene species generated by treatment of 4-phenylthiooxazolidin-2-ones (8a-c) with tri-n-butyltin hydride in the presence of azobisisobutyronitrile (AIBN). Conversion of 9a to cis-octahydro-2, 5-dimethyl-4a-phenylcyclopenta[c]pyridine (19) was successfully achieved via a route involving ring cleavage of the oxazolidinone ring of 9a, oxidation of hydroxymethyl group, and decarbonylation.View full abstractDownload PDF (741K) -
TAKASHI YOSHIDA, LING CHEN, TETSURO SHINGU, TAKUO OKUDA1988 Volume 36 Issue 8 Pages 2940-2949
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new dimeric dehydroellagitannins, named euphorbin A (6) and euphorbin B (7), were isolated from the aerial parts of Euphorbia hirta, and their structures, containing 4C1 and 1C4 glucopyranose residues and a dehydrohexahydroxydiphenoyl group, were elucidated on the basis of chemical and spectral studies. Five monomeric hydrolyzable tannins, i.e., 2, 4, 6-tri-O-galloyl-D-glucose, 1, 3, 4, 6-tetra-O-galloyl-β-D-glucose, 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose, geraniin and terchebin, as well as two quinic acid esters, i.e., 5-O-caffeoylquinic acid and 3, 4-di-O-galloylquinic acid, and three flavonol glycosides were also isolated.View full abstractDownload PDF (944K) -
MAYUMI KOYAMA, MIHOKO TAMURA, AKIRA ANDO, TAKABUMI NAGAI, TAKUICHI MIK ...1988 Volume 36 Issue 8 Pages 2950-2954
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs the extension of our research to find a biologically active analogue of vitamin E, a more convenient method for the synthesis of fluorine derivatives of 6-chromanol than our previous method was developed. Thus, 2-(3-chloropropyl)-2, 5, 7, 8-tetramethyl-6-chromanol (3) was synthesized by the reaction of 6-chloro-3-methyl-2-hexen-1-ol (2) and trimethylhydroquinone, and the phosphonium ylides (5 and 6) derived from 3 were condensed with trifluoromethylated ketones to give 2-(trifluoroprenyl)-6-chromanol compounds (1a, 1b and 1c) by means of the Wittig reaction as modified by Schlosser. By the use of this revised procedure, the total yields of the chromanols were much improved. Further, the modified Wittig reaction showed higher stereoselectivity than the previous syntheses of these compounds. The double bonds of the side-chain of the products were reduced to give fluorine derivatives of tocopherol analogues. Compound 3 was found to be a useful intermediate for the facile synthesis of vitamin E derivatives.View full abstractDownload PDF (572K) -
NOBUO OGAWA, TOSHIHIKO YOSHIDA, TAKAYUKI ARATANI, EIICHI KOSHINAKA, HI ...1988 Volume 36 Issue 8 Pages 2955-2967
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of developing new atiulcer agents, a series of 4-quinazolinone derivatives was synthesized and tested for histamine H2-antagonist activity and gastric antisecretory activity. Thus, 2-alkylamino- (8a-d, 10a-s), 2-alkylthio- (15), and 2-alkyl-4-quinazolinones (18a-k) were prepared by the condensation of alkylamines with 2-chloro- or 2-methlthio-4-quinazolinones, the condensation of alkyl bromides with 2-mercapto-4-quinazolinones, and the condensation of alkylcarboxylic acids with anthranilamides, respectively.Several of the 4-quinazolinone derivatives thus synthesized showed potent H2-antagonist activity, and one of them, 2-[3-[3-(1-piperidinylmehyl)phenoxy]propylamino]-4(3H)-quinazo-linone (8d) showed the most potent antisecretory activity. The structure-activity relationships are discussed.View full abstractDownload PDF (1065K) -
MUNEFUMI KANAO, YOSHIFUMI WATANABE, YOUICHI KIMURA, HIDEYUKI KANNO, HI ...1988 Volume 36 Issue 8 Pages 2968-2976
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBasic N-heteroaromatic derivatives (1, 2, 4-triazole, thiazole and pyrimidine derivatives) having a 2-[4-(carboxy)phenoxy]ethyl moiety or a 4-[2-(carboxy)vinyl]benzyl moiety were prepared, and evaluated for ability to inhibit thromboxane A2 (TXA2) synthesis. Among the compounds prepared in this study, the 5-substituted thiazole derivatives 14d, 27 and 28 were more potent inhibitors of TXA2 production than the corresponding imidazole derivatives, and the 1-substituted 1H-1, 2, 4-triazole derivatives 14a and 15a were almost as potent as the corresponding imidazole derivatives.View full abstractDownload PDF (892K) -
KIMIYE BABA, KAORU MAEDA, YUKO TABATA, MITSUNOBU DOI, MITSUGI KOZAWA1988 Volume 36 Issue 8 Pages 2977-2983
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new polyphenols, cassigarol A and cassigarol B, have been isolated from the heartwood of Cassia garrettiana CRAIB. (Thai drug "sa mae sarn, " Leguminosae). The structures of cassigarol A and cassigarol B were determined by means of chemical studies and spectral and X-ray analyses.View full abstractDownload PDF (614K) -
HIROSHI MORITA, NOBUO TOMIOKA, YOICHI IITAKA, HIDEJI ITOKAWA1988 Volume 36 Issue 8 Pages 2984-2989
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAutooxidation and photosensitized oxidation converted guaia-6, 9-diene into hanalpinol, both compounds are contained in the rhizomes of Alpinia japonica. This process may be considered to be a biomimetic conversion. Guaia-6, 9-diene may be regarded as an immediate precursor of hanalpinol, and a biogenetic pathway has been proposed. The results of molecular orbital calculation (modified neglect of differential overlap (MNDO) method) supported this proposal and provided a basis for conformational analysis.View full abstractDownload PDF (569K) -
ISAO KOUNO, TOSHIHIKO AKIYAMA, NOBUSUKE KAWANO1988 Volume 36 Issue 8 Pages 2990-2992
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo sequiterpene lactones, 6-deoxypseudoanisatin and a new compound have been isolated from the seeds of Japanese star-anise along with three known compounds, anisatin, neoanisatin, and pseudoanisatin. The new compound was named 6-deoxymajucin and its structure was deduced by spectral studies.View full abstractDownload PDF (368K) -
SHIGEO IKEGAWA, TAKAO KUROSAWA, MASAHIKO TOHMA1988 Volume 36 Issue 8 Pages 2993-2999
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the metabolic fate of equine estrogens, 2-hydroxyequilin, 2-hydroxy-equilenin and their isomeric monomethyl ethers were synthesized as authentic specimens. Vanillin and isovanillin were employed as starting materials leading to the desired β-ketosulfoxides (2a, b). Condensatin of the α, β-unsaturated ketones (4a, b) obtained by thermal elimination of 3a and 3b with 2-methylcyclopentane-1, 3-dione provided the triketones (5a, b), which were cyclized to the estrapentens (6a, b). Several oxido-reduction reactions were then performed to give the title compounds (8, 13).View full abstractDownload PDF (853K) -
KAZUKI AKIRA, SHIGEO BABA, SHOICHI AOKI1988 Volume 36 Issue 8 Pages 3000-3007
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA specific radio-gas chromatographic method for the quantitative analysis of [14C]nifedipine and its metabolite in hamster plasma is described. Nanogram amounts of nifedipine could be precisely analyzed without any thermal decomposition using a column packing of 1.5% OV-1. The usefulness of this method was demonstrated by tracing the time course of plasma concentration of nifedipine and its pyridine metabolite following intravenous administration to hamsters. Nifedipine plasma levels as low as 5 ng/ml could be measured by using the labeled compound synthesized in the present study.View full abstractDownload PDF (739K) -
NAM-HO CHOI, MOTOWO TOMITA1988 Volume 36 Issue 8 Pages 3008-3011
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRabbit factor H, a regulatory protein of complement, has a blocked N-terminus. After treatment with pyroglutamyl aminopeptidase, its N-terminus could be determined. The C-terminus of rabbit factor H was determined to be tyrosine by carboxypeptidase A treatment. The peptides produced by cyanogen bromide cleavage were purified by gel chromatography, followed by highperformance liquid chromatography. The N-terminal sequences of eight peptides thus purified were analyzed. When the sequence determined in this study was compared with that of mouse factor H derived from the complementary deoxyribonucleic acid (cDNA) sequence, which has recently been reported by Kristensen and Tack, 100 of the 167 residues were identical with those of mouse factor H (about 60% homology).View full abstractDownload PDF (470K) -
HARUKI OISHI, MASAJI FUSAMOTO, YASUMICHI HATAYAMA, MASAKAZU TSUCHIYA, ...1988 Volume 36 Issue 8 Pages 3012-3019
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn automated analysis system for evaluating reaction kinetics between Limulus amebocyte lysate (LAL) and endotoxin has been developed by using a data acquisition program for the Toxinometer. This program collects the time-course data of turbidity change in gel-clotting in the LAL-endotoxin reaction, determines the gelation time, and calculates endotoxin concentration of up to 64 samples simultaneously and independently. Whole time-course data obtained at 12s increments are displayed on a monitor and reported on a printer both graphically and numerically. LAL-endotoxin reaction kinetics depending upon different LAL preparations or inhibitory or enhancing effects of chemicals, were analyzed with this system by observing the reaction time-course data. By selecting variable threshold values for gelation detection of this program, well correlated standard curves of endotoxin concentration were obtained. Furthermore, by introducing parameters related to the reaction to the reaction kinetics, gel formation induced by β-1, 3-glucan could be distinguished from that by endotoxin, which was impossible with the conventional gel-clot method.View full abstractDownload PDF (685K) -
SADAKI FUJIMOTO, KAZUKI MURAKAMI, AKIRA ISHIKAWA, KENJI HIMI, AKIRA OH ...1988 Volume 36 Issue 8 Pages 3020-3026
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo forms, acid phosphatases A and B (APases A and B), of low-molecular-weight APases were highly purified. APases A and B showed isoelectric points ofapproximately 5.9 and 5.4, respectively, and the apparent molecular weights were estimated to be 15000 by Sephadex G-75 gel filtration or 14500 and 14000, respectively, by sodium dodecyl sulfate/polyacrylamide-gel electrophoresis. Both enzymes catalyzed the hydrolysis of p-nitrophenyl phosphate, phosphotyrosine, and flavin mono-nucleotide, but APase A showed higher activity with lower Km value than APase B toward phosphotyrosine. APase B was effectively activated by purine compounds, whereas APase A was not. Some differences in sensitivity to inhibitors between APases A and B were also observed. These enzyme forms also existed in kidney, brain, and erythrocytes of the rat.View full abstractDownload PDF (830K) -
ATSUSHI HIRAOKA, JUNKO OHTAKA, SATORU KOIKE, YUKO TSUBOI, SHINPEI TSUC ...1988 Volume 36 Issue 8 Pages 3027-3031
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inhibitory effects of twelve oxime compounds on the activity of bovine serum monoamine oxidase (copper-containing amine oxidase, E.C. 1.4.3.6) were assayed in vitro. The most potent inhibitor among the compounds examined was 2-butanone oxime, of which the 50% inhibiting concentration in the reaction mixture was 7×10-6 M. Acetone oxime, acetoaldehyde oxime, salicylaldehyde oxime and formamide oxime were less potent inhibitors, while 2, 3-butanedione monooxime, 2, 3-butanedione dioxime, D-camphor oxime, α-furil dioxime, pyridine-2-aldehyde oxime, pyridine-4-aldehyde oxime, syn-2-pyridialdehyde oxime and di-2-pyridiketone oxime exhibited virtually no inhibitory effect on the enzyme activity. The type ofinhibition by 2-butanone oxime was non-competitive, and the inhibitor constant and Km value with respect to allylamine as the substrate were estimated graphically to be 6.7×10-6 and 3.9×10-4 M, respectively.View full abstractDownload PDF (558K) -
TADASHI KIHO, MASAHIKO ITO, KATSUYUKI NAGAI, CHIHIRO HARA, SHIGEO UKAI1988 Volume 36 Issue 8 Pages 3032-3037
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA water-soluble polysaccharide (CI-5N), [α]D +30°in water, was isolated from the alkaline extract of the insect-body portion of Chan hua (Chinese name) (fungus : Cordyceps cicadae). CI-5N was homogeneous on gel filtration and gave a single spot on glass-fiber paper-electrophoresis. It was composed of d-mannose, D-galactose, and D-glucose in the molar ratio of 1.0 : 0.67 : 0.23, and was free from protein. The molecular weight was estimated by gel fitration to be ca. 39000. The polysaccharide had affinity for concanavalin A. From the results of methylation analysis Smith degradation, stepwise hydrolysis, and carbon-13 nuclear magnetic resonance, it was concluded that the polysaccharide has a highly branched structure, and is composed of (1→6)-linked and (1→2)-linked α-D-mannopyranosyl residues, and (1→2)-linked α-D-glucopyranosyl residues. Some of the D-mannopyranosyl residues are present as branching points of (1→2, 6)-linkage, and the branches contain short chains having (1→2)-linked β-D-galactofuranosyl residues and single β- and/or α-D-galactofuranosyl residues.View full abstractDownload PDF (691K) -
KAZUNOBU MIURA, TEIJI ITOH, TOHRU NAKAMURA, JIRO KOYAMA, TOHRU UEDA, E ...1988 Volume 36 Issue 8 Pages 3038-3042
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMonoclonal antibodies specific for ribonuclease inhibitor (RNasin) were obtained by the method of production of hybridomas from spleen cells and myeloma cells. The specificity of monoclonal antibodies obtained by cloning was investigated by Western blot analysis. The addition of ribonuclease (RNase) A to RNasin resulted in the inhibition of antibody binding to the antigen. However, the addition of RNase A to the antigen-antibody complex did not cause dissociation of the complex.View full abstractDownload PDF (638K) -
TERUAKI AKAO, YUE-ZHONG SHU, YOKO MATSUDA, MASAO HATTORI, TSUNEO NAMBA ...1988 Volume 36 Issue 8 Pages 3043-3048
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPaeoniflorin from peony roots was converted to new compounds in the presence of various sulfhydryl compounds by Lactobacillus brevis. The compounds formed in the presence of 3-mercaptopropionic acid, 2-mercaptoethanol and thiobenzoic acid were determined to be 7R and 7S mixture of 8-(2-carboxyethylthio)paeonimetabolin I, 8-(2-hydroxyethylthio)paeonimetabolin I and 8-benzoylthiopaeonimetabolin I, respectively, by various spectroscopic methods. These compounds are adducts of a metabolic intermediate of paeoniflorin with the sulfhydryl compounds.View full abstractDownload PDF (675K) -
YOSHIO SEKIGAWA, YOSHIKO SONODA, YOSHIHIRO SATO1988 Volume 36 Issue 8 Pages 3049-3054
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetabolism of 32-hydroxylated 24, 25-dihydrolanosterols (1-3), including the intermediate of lanosterol and 24, 25-dihydrolanosterol (4, DHL) demethylation, were studied in a reconstituted system consisting of rat liver partially purified cytochrome P-450, which catalyzes lanosterol 14-demethylation (cytochrome P-45014DM), and reduced nicotinamide adenine dinucleotide phosphate (NADPH)-cytochrome P-450 reductase. The reconstituted system converted lanost-8-ene-3β, 32-diol (1) to 4, 4-dimethyl-5α-cholesta-8, 14, dien-3β-ol (5), the 14-dehydroxymethylated product, in the same way as 4. Lanost-7-ene-3β-32-diol (2) and lanost-6-ene-3β, 32-diol (3), the isomers of 1, were not converted to the corresponding 14-dehydroxymethylated products. The apparent Km value of cytochrome P-45014DM for 1 was about 1/6 of that for 4. The metabolism of 4 was inhibited by 7-oxo-24, 25-dihydrolanosterol (6, 7-oxo-DHL), which is a potent inhibitor of cholesterol biosynthesis from lanosterol or 4. However, the metabolism of 1 was less inhibited by 6 than that of 4.View full abstractDownload PDF (595K) -
TAKESHI IGAWA, YOSHIE MAITANI, YOSHIHARU MACHIDA, TSUNEJI NAGAI1988 Volume 36 Issue 8 Pages 3055-3059
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman interferon-β (HuIFN-β) titer after intransal administration was determined by enzyme immunoassay (EIA), substituting for bioassay. The intranasal absorption was linearly related to HuIFN-β dose. Compared with intravenous administration, the mean bioavailability of intranasal HuIFN-β was 3%. The effects of several excipients, human serum albumin (HSA), polyethylene glycol, diethylaminoethyl-dextran, carboxy polymethylene, α-cyclodextrin and cholesteryl stearate, on the absorption of HuIFN-β were examined with the powder dosage form. Among these excipients, HSA and α-cyclodextrin gave the highest HuIFN-β concentrations in plasma. The area under the plasma concentration-time curve (AUC) decreased as the molecular weight of excipients was increased.View full abstractDownload PDF (488K) -
YUJI TOKUNAGA, TOMOAKI IWASA, JIRO FUJISAKI, SEIJI SAWAI, AKIRA KAGAYA ...1988 Volume 36 Issue 8 Pages 3060-3069
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1a-N-Stearoyl mitomycin C (MMC) and six 1a-N-substituted derivatives of MMC possessing the cholesteryl moiety with different spacers were synthesized, and their biopharmaceutical properties were studied to assess the feasibility of such derivatives as prodrugs for intravenously injectable liposomal sustained-release carrier systems. All compounds showed increased lipophilic indices (logk'0) in high performance liquid chromatography. It was found that all the derivatives could be almost completely entrapped in liposomes, although MMC itself was hardly encapsulated. The derivatives with the exception of cholesteryloxycarbonyl MMC (II) and N-(cholesteryloxy-carbonyl)-4-aminophenylacetyl MMC (VI) were converted to the parent drug in rat serum. The suceptibility of the compounds to hydrolysis was strongly affected by the spacer structure between MMC and the cholesteryl moiety. Cholesteryloxyacetyl MMC (IV) was converted to MMC mainly by chemical hydrolysis. N-(Cholesteryloxycarbonyl)glycyl MMC (III) was also hydrolyzed to MMC chemically but in this case hydrolysis was accelerated in the presence of mouse, rat and human serum. No species differences were observed in these bioactivation phenomena. Entrapment of derivatives III and IV in liposomes resulted in enhancement of the stability against both chemical and enzymatic hydrolysis. The derivatives possessing the cholesteryl moiety were firmly associated with liposomes in the circulation, while stearoyl MMC (VIII) was rapidly recoved. These results suggest that derivatives III and IV have the potential to be utilized as lipophilic prodrugs for liposomal sustained-release carrier systems to be delivered by intravenous injection.View full abstractDownload PDF (1015K) -
YOSHINOBU FUKUMORI, YUMIKO YAMAOKA, HIDEKI ICHIKAWA, YOSHKAZU TAKEUCHI ...1988 Volume 36 Issue 8 Pages 3070-3078
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAqueous dispersions of ethyl acrylate (EA)-methyl methacrylate (MMA)-2-hydroxyethyl methacrylate (HEMA) copolymers were developed to produce microcapsules with a pH-independently water-insoluble membrane by the Wurster process. The dispersions were prepared by an emulsion polymerization technique. The resin dry weight content of the dispersion was 21-23%. Lactose (328μm) and phenacetin were used as drug models.The mole ratios of EA, MMA and HEMA used were 12 : 6 : X, 9 : 9 : X and 6 : 12 : X (X=4, 6, 8). An incrase in MMA content raised the softening temperature of the membrane. HEMA affected it far less than MMA, but remarkably enhanced the release of lactose in JPXI disintegration 2nd fluid (pH 6.8).The delayed release of lactose, characterized by a lag time and subsequent rapid release, was observed most clearly for the microcapsules prepared with EA-MMA-HEMA (9 : 9 : 4) copolymer. When the lactose microcapsules contained phenacetin and polyvinylpyrrolidone (PVP), PVP did not affect the lag time, but remarkably enhanced the release of lactose after the lag time. Phenacetin was also released in a similar manner.From the expansion of the particles in the dissolution fluid, it was estimated that the lag time corresponded to the time needed for the membrane to be hydrated, and the subsequent rapid release resulted from the permeability change caused by hydration and the reduction in membrane thickness due to the particle expansion by taken-up water. Polyvinylpyrrolidone contained within microcapsules enhanced the water intake, which induced bursing ofthe membrane.View full abstractDownload PDF (764K) -
PAUL MCGOFF, ANTONIA C. BAZIOTIS, RICHARD MASKIEWICZ1988 Volume 36 Issue 8 Pages 3079-3091
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCovalent conjugation of bovine erythrocyte superoxide dismutase (SOD) with activated polyethylene glycol (PEG) results in a mixture of modified species (PEG-SOD) with properties different from those of the native enzyme. The components of this mixture were resolved by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), isoelectric focusing, and chromatographic (size-exclusion, anion-exchange, cation-exchange and reverse-phase high performance liquid chromatography) techniques. Physicochemical properties such as apparent molecular weight, isoelectric point, relative hydrophobicity and relative cation-anion charge number were measured by electrophoretic and chromatographic procedures. Dispersity and apparent radius were examined by chromatographic and light scattering techniques. The extent of covalent modification and enzymatic activity change were measured by chemical and spectroscopic methods, showing that activity loss was not due to catalytic site modification. The properties of the PEG-modified form of the enzyme were compared with those of native SOD and showed that in addition to changing biological properties, PEG modification of proteins can result in a product with unexpectedly high heterogeneity and substantial changes in isoelectric point and hydrophobicity. Altered biological properties may therefore not merely be due to shielding of protein surface by PEG chains. Apparent properties of PEG modified proteins such as molecular weight were found to be highly method dependent, with poor agreement being shown among classical measurements.View full abstractDownload PDF (1400K) -
TAKUYA OKAGAKI, HIROSHI YOSHIKAWA, KANJI TAKADA, SHOZO MURANISHI1988 Volume 36 Issue 8 Pages 3092-3097
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antitumor effect of aclarubicin (ACR) in an oily dosage formulation composed of Lipiodol (lymphographic oil), or with linoleic acid and 1-dodecylazacycloheptan-2-one (Azone), was investigated by hepatic intra-arterial administration against Walker 256 carcinosarcoma implanted in the rat liver. Evaluation based on the grown rate of the tumor indicated that ACR was more effective on administration as Lipiodol solution or oil-in-water emulsion compared to saline aolution, but the addition of linoleic acid or Azone to Lipiodol solution did not further improve the antitumor activity of ACR. A clear correlation between the depression of the hepatic tumor growth rate and the levels of ACR and its active metabolites in the tumor tissue 24h after the hepatic intra-arterial administration was also observed.View full abstractDownload PDF (606K) -
YUKIHITO SASAKI, MASANOBU HORIE, SHIGEO BABA1988 Volume 36 Issue 8 Pages 3098-3104
Published: August 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDesipramine (DMI), a metabolite of imipramine (IP), has approximately the same antidepressant activity as the mother compound. It is important to clarify the fractional ratio of metabolism from IP to DMI (fmIP-DMI). We have developed a new technique to estimate fmIP-DMI by the use of a co-administration technique. After co-administration of a mixture of IP-d4 and DMI-d0 to rats, area under the plasma concentration-time curve (AUC) and renal excretion of DMI-d4 and DMI-d0 were examined. fmIP-DI estimated from the ratio of AUC of DMI-d4 to that of DMI-d0 was almost the same as fmIP-DMI calculated from the ratio of the amount of excreted DMI-d4 to that of DMI-d0. This means that fmIP-DMI can be calculated by using the renal excretion data instead of AUC. The relationship between fmIP-DMI and IP-d4 dose is also discussed.View full abstractDownload PDF (607K)