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Volume 31, Issue 5
Displaying 1-50 of 62 articles from this issue
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HIDEO KANEKO, SADAO HIROTA1983 Volume 31 Issue 5 Pages 1445-1459
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDielectric relaxation due to the interfacial polarization of emulsions of water in a hydrophobic colloidal silica-oil gel (W/(S·O) emulsion, below) was investigated over a wide range of volume fraction of dispersed phase at frequencies ranging from 10kHz to 3MHz. W/(S·O) emulsions without surfactant showed a dielectric relaxation, and the limiting dielectric constants at high and low frequencies were both shown to satisfy the equations given by Wagner's theory1, 2) up to a water volume fraction as high as 0.65. In W/(S·O) emulsions without surfactant, absence of any aggregation of water particles was ascertained by microscopic observation, while aggregation was observed in W/(S·O) emulsions with nonionic surfactant. In emulsions with aggregation, the limiting dielectric constant at low frequencies deviated from both Wagner's and Hanai's theoretical curves, though the limiting dielectric constant at high frequencies was consistent with Hanai's theoretical curve. The dielectric anomaly, i.e. the deviation from the theoretical values at low frequencies, may be related to the particle aggregation of w/o emulsions, and it may be possible to make a quantitative evaluation of the colloid-chemical stability of w/o emulsions in terms of particle aggregation.View full abstractDownload PDF (3290K) -
MASARU SAITO, YOSHINORI HARADA, KUGAKO MATSUMURA, HIDEO KATO, YASUO IT ...1983 Volume 31 Issue 5 Pages 1460-1468
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structures of the two crystalline forms (I and II) of α-[(tert-butylamino)-methyl]-2-chloro-4-hydroxybenzyl alcohol hydrochloride (HOKU-81), which is one of the metabolites of tulobuterol hydrochloride (C-78) and a potent β2-adrenergic stimulant, have been determined by X-ray structure analysis. The structures were solved by direct methods and refined by the block-diagonal least-squares method including anisotropic thermal parameters to final R values of 0.051 and 0.050 for Forms I and II, respectively. The molecular conformations in the two forms are similar, but nevertheless the crystal structures are very different. In Form I, independent hydrogen bonds of four types are formed, while three types of independent hydrogen bond are formed in Form Ii, producing characteristic molecular sheets in the crystals. Comparison of the crystal structures of the polymorphs between HOKU-81 and C-78 indicates that some of the differences of physico-chemical properties are attributable to the differences of crystal packings. Furthermore, comparison of the molecular conformations of HOKU-81 and C-78 with those of the other adrenergic agents having an ethanolamine side chain shows that these compounds have homologous conformations in the aliphatic side chain.View full abstractDownload PDF (663K) -
MASAHIDE NOJI, SHIGERU MOTOYAMA, TAZUKO TASHIRO, YOSHINORI KIDANI1983 Volume 31 Issue 5 Pages 1469-1473
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHalogeno, sulfato, and nitrato Pt (II) complexes of 2, 3-diaminopropanol (pnOH) isomers were synthesized and their antitumor activities against leukemia L1210 were tested. The conformations of their chelate rings were determined to be λ-and δ-gauche forms for R- and S-pnOH, respectively, by 13C-nuclear magnetic resonance and circular dichroism spectral analyses. Among the pnOH isomers, Pt (II) complexes containing R-pnOH showed higher antitumor activity than those containing S- or racemic pnOH. It seems that there may be a relationship between the conformations of the chelate rings and antitumor activity in the case of five-membered chelate rings.View full abstractDownload PDF (566K) -
SEITARO SAEKI, HARUYOSHI HONDA, MASATOMO HAMANA1983 Volume 31 Issue 5 Pages 1474-1481
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Methyl- and N-benzylhydroxylamine reacted smoothly with ethyl acetoacetate to afford the pyrroline compounds 1 and 2, respectively. On the other hand, the reaction of N-cyclohexylhydroxylamine gave the nitrone compound 3. Other active methylene compounds, i.e., diethyl acetonedicarboxylate, benzoylacetone and nitroacetone, reacted with methylhydroxylamine to give the N-methylpyrrole 6, the nitrone 7 and the isoxazoline 8, respectively.View full abstractDownload PDF (672K) -
NARIAKIRA MIZOKAMI, HIROSHI FUKASE, SATOSHI HORII, YUTAKA KUWADA1983 Volume 31 Issue 5 Pages 1482-1493
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereoselective synthesis of 2α-methyl-and 2β-methyl-3-(substituted methyl)-cephalosporins via 2-methyl-3-formyloxymethylceph-2-em (5) and 2-methyl-3-acetoxymethylceph-2-em (16) from 2-methylene-3-acetoxymethylcephalosporin (1) is described. Reduction of 1 with zinc in acetic acid gave 2, 3-dimethylenecepham (2), while reduction with zinc in formic acid gave 5 and reduction with sodium borohydride gave 16. Hydrolysis of 5 gave 2-methyl-3-hydroxymethylceph-2-em (6), which was stereoselectively converted via 2-methyl-3-(heterocyclic thiomethyl) ceph-2-em (8) and 2-methyl-3-formyl-ceph-2-em (12) into the corresponding 2α-methyl-3-(substituted methyl) ceph-3-ems by oxidation with peracid. On the other hand, isomerization of 16 to the corresponding ceph-3-em by oxidation with peracid gave mainly the 2β-methyl isomer (55 : 1 ratio). Ozonolysis of 2 followed by treatment with diazomethane gave 2-oxo-3-methoxyceph-3-em (24).View full abstractDownload PDF (1353K) -
TADAYUKI KURAISHI, TAKAO TANIGUCHI, TAKAO MURAKAMI, NOBUTOSHI TANAKA, ...1983 Volume 31 Issue 5 Pages 1494-1501
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Microlepia marginata (PANZER) C. CHR. five new ent-kaurane type diterpene glycosides, microlepin (I), 17-O-acetylmicrolepin (VIII), 6'-O-acetylmicrolepin (IX), 4-epi-microlepin (X) and 6'-O-α-L-rhamnopyranosyl-4-epi-microlepin (XVIII) were isolated and their structures were elucidated by spectroscopic methods and some chemical reactions. Microlepin and 4-epi-microlepin possesses the structures 16α, 17, 19-trihydroxy-ent-kaurane 19-O-β-(4'-O-methyl)-D-glucopyranoside and 16α, 17, 18-trihydroxy-ent-kaurane 18-O-β-(4'-O-methyl)-D-glucopyranoside.View full abstractDownload PDF (931K) -
TAKAO MURAKAMI, NOBUTOSHI TANAKA, YUKIO KOMAZAWA, YASUHISA SAIKI, CHIU ...1983 Volume 31 Issue 5 Pages 1502-1504
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn addition to compounds already isolated, reinvestigation on the constituents of Pteris purpureorachis COPEL has led to the isolation of new ent-atisane derivatives, which turned out to be 9, 11β-epoxy-15-oxo-ent-atis-16-en-19-oic acid (IV) and i.s 19-β-D-glucopyranosylester (V). The structures were elucidated by spectroscopic methods and chemical investigations.View full abstractDownload PDF (457K) -
YUJI MORI, SHIGERU FUJIWARA, TOSHIKO MIYACHI, HIROYUKI KITANISHI, MASA ...1983 Volume 31 Issue 5 Pages 1505-1517
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe electron ionization mass spectra (MS) of S-methylated derivatives of N-(2-mercapto-2-methylpropanoyl)-L-cysteine and 2-alkylthio-2-methylpropanoic acids, as well as their esters and amides, were examined. Use of the deuterium labeling technique and accurate mass measurement supported the proposed fragmentation pathways. Extensive loss of CH2S from a molecular ion by the McLafferty rearrangement of a primary hydrogen is important in the MS of S-methyl compounds of amide derivatives. It was demonstrated that the intensity of the rearrangement ion decreases in the order of amide, ester, and acid, and in the case of amides the rearrangement is suppressed by the nonbonded interaction between methyl groups on the α carbon and the amide nitrogen.View full abstractDownload PDF (1070K) -
KIMIO KATSUURA, KEIICHI YAMAGUCHI, SHINICHIRO SAKAI, KEMMOTSU MITSUHAS ...1983 Volume 31 Issue 5 Pages 1518-1527
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyanomethylation of 4, 5, 6, 7-tetrahydro-6, 6-dimethyl-7-oxobenzothiazole (VII), which was prepared from 4, 4-dimethyl-1, 3-cyclohexanedione (I) in several steps, afforded the cyano alcohol (VIII). Compound VIII was treated with lithium aluminum hydride and the resulting amino alcohol (IX) was converted into 7-(2-aminoethyl)-4, 7-dihydro-6, 7-dimethylbenzothiazole (XI) by Wagner-Meerwein rearrangement. Reaction of XI with bromine gave the salt (XII). Treatment of XII with potassium carbonate produced the bridged aziridine (XIII), which was cleaved to the thiazolo [5, 4-f] morphan (4, 5, 6, 7, 8, 9-hexahydro-5, 9-methanothiazolo [4, 5-d] azocine) derivative (XVI) by the action of benzoyl bromide. Dehydrobromination followed by hydrolysis of the benzoyl group led XVI to 5-methyl-9-methylenethiazolo [5, 4-f] morphan (XVIII). Stereospecific hydrogenation of XVIII yielded the 9α-methyl isomer (XIX), whose N-methylation by the Eschweiler-Clarke method completed the synthesis of the desired thiazolo [5, 4-f] morphan (XX). The molecular structure of the oxalate of XIX was established by X-ray analysis.View full abstractDownload PDF (1082K) -
KEIICHI NITTA, NORITAKA FUJITA, TADASHI YOSHIMURA, KUNIZO ARAI, YUZURU ...1983 Volume 31 Issue 5 Pages 1528-1533
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new derivatives of butyrolactone I were isolated from Aspergillus terreus IFO 4100, and the structures were determined. A metabolic pathway from phenylalanine to butyrolactone I was established by administration of potential intermediates to growing or resting cells of Aspergillus terreus IFO 8835 and by enzymatic studies. Three enzymes involved in the biosynthesis were identified.View full abstractDownload PDF (757K) -
EIKO OHTSUKA, AKIO YAMANE, MORIO IKEHARA1983 Volume 31 Issue 5 Pages 1534-1543
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2'-O-Tetrahydrofuranyl nucleosides have been synthesized from 2, 3-dihydrofuran via 3', 5'-bis-tert-butyldimethylsilylnucleosides. These nucleosides were used as intermediates for oligonucleotide syntheses by the phosphotriester method. Trimers C-C-A and C-C-U were synthesized by the stepwise addition of monomers. U-U-U-U-U-U, A-U-G-A-U-G and A-U-G-A-U-G-A-U-G were obtained by the block condensation of trimers in which the 5'-hydroxyl group had been selectively phosphorylated.View full abstractDownload PDF (1057K) -
MASANORI KUROYANAGI, TADATAKA NORO, SEIGO FUKUSHIMA, RITSUO AIYAMA, AK ...1983 Volume 31 Issue 5 Pages 1544-1550
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new diarylheptanoids [(5R)-trans-1, 7-diphenyl-5-hydroxy-6-hepten-3-one (VIIa), (3S, 5S)-trans-1, 7-diphenyl-3, 5-dihydroxy-1-heptene (VIIIa), trans-1, 7-diphenyl-5-hydroxy-1-heptene (IX) and trans, trans-1, 7-diphenyl-5-hydroxy-4, 6-heptadien-3-one (Xa)] have been isolated from the seeds of Alpinia katsumadai HAYATA, together with trans, trans-farnesol (I), trans-cinnamaldehyde, three flavonoids [alpinetin (II), cardamomin (III) and pinocembrin (IV)], and two known diarylheptanoids [(3S, 5R)-3, 5-dihydroxy-1, 7-diphenylheptane (V) and trans, trans-1, 7-diphenyl-4, 6-heptadien-3-one (VI)], and their structures were determined on the basis of chemical and spectral evidence. This is the first time that trans-cinnamaldehyde, IV, V and VI have been isolated from these seeds.View full abstractDownload PDF (975K) -
TAKESHI IMANISHI, MAKOTO INOUE, YASUAKI WADA, MIYOJI HANAOKA1983 Volume 31 Issue 5 Pages 1551-1560
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESScis-3, 4-Disubstituted piperidine compounds (2 and 3) were stereoselectively prepared from benzyl 3-(1, 3-dioxolan-2-ylmethyl)-1, 2, 3, 6-tetrahydropyridine-1-carboxylate (13) via the ketone (17). A total synthesis of (±)-corynantheidol (4) and a formal synthesis of (±)-quinine (5) have also been achieved from the piperidines 2 and 3, respectively.View full abstractDownload PDF (1012K) -
TOSHIKI MUTO, JUN TANAKA, TOSHIAKI MIURA, MICHIYA KIMURA1983 Volume 31 Issue 5 Pages 1561-1566
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe autoxidation of cholesterol in a benzene solution of egg lecithin and Fe (acac)3, giving products variously oxygenated in the steroidal ring B, proceeded with consumption of the unsaturated long-chain fatty acid moieties, particularly C18 : 2, in the lecithin molecule. The reaction showed a marked β-stereoselectivity of epoxidation and was inhibited by a radical scavenger (BHT). Cholesterol was highly susceptible to ferric iron-catalyzed autoxidation within liposomes prepared by using egg lecithin. The oxidative degradation of the unsaturated moieties, C18 : 1, and C18 : 2, in the lecithin led to allylic oxidation as well as the β-stereoselective epoxidation of cholesterol. A radical scavenger inhibited both the degradation of these moieties and the oxygenation of cholesterol. The oxygenation was retarded in liposomes prepared by using saturated dipalmitoyl lecithin, and was dominated by allylic oxidation giving cholesteryl hydroperoxide as the main product. Cholesterol in the liposomes containing egg lecithin was, thus, assumed to be co-oxidized with the unsaturated fatty acid moieties by the radical pathway, when the liposomes were autoxidized in the presence of ferric catalyst.View full abstractDownload PDF (623K) -
MASAAKI KATAI, TADAMASA TERAI, HARUO MEGURI1983 Volume 31 Issue 5 Pages 1567-1571
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight triterpenoids and a sterol were isolated from the bark of Pieris japonica D. DON (Japanese name : asebi, Ericaceae) and have been elucidated as 3β-acetoxyurs-11-en-28, 13-olide, 3β-acetoxy-12α-hydroxyolean-28, 13-olide, 3β-acetoxy-28-hydroxyurs-12-ene, 3β, 28-dihydroxyurs-12-ene, 3β-acetoxyurs-12-en-28-al, taraxeryl acetate, taraxerol, taraxerone and β-sitosterone by a combination of chemical and spectroscopic studies. 13C Nuclear magnetic resonance spectral analysis of several γ-lactones of the ursane and oleanane series was undertaken, and all the carbons were assigned by means of single frequency off-resonance and selective decoupling methods and by comparison of the signals with those of methyl esters of acetyl ursolic acid and acetyl oleanolic acid.View full abstractDownload PDF (642K) -
SHIGERU OZASA, YASUHIRO FUJIOKA, JUNICHIRO KIKUTAKE, EIICHI IBUKI1983 Volume 31 Issue 5 Pages 1572-1581
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNine polyphenyls, including six new compounds, 3'-phenyl-o-quaterphenyl (3), 2, 6-diphenyl-m- (4), 2, 6-diphenyl-p-terphenyl (5), 2, 6, 5'-triphenyl-m-terphenyl (6), 2', 2"-diphenyl-m-quaterphenyl (8), and 2'-(phenyl-d5)-m-terphenyl (9), were synthesized by the Ullmann coupling reaction of aryl iodide (s) or by the Kharash-type coupling reaction of deuterated aryl Grignard reagent with aryl iodide catalyzed by bis (acetylacetonato)-nickel (II). Infrared studies of the polyphenyls showed that the range of 730-770 cm-1, generally accepted as the position of the C-H out-of-plane bending bands of phenyl rings, should be widened slightly to 730-781 cm-1. The high frequency bands were found to be correlated closely to the sterically overcrowded structure of terminal rings. Proton magnetic resonance spectral studies indicated that the characteristic spectral features of the polyphenyls containing 1, 2, 3-trisubstituted ring (s) were fully consistent with their conformational aspects deduced from stereomodels. Ultraviolet spectral data suggested that the most probable conformation of the highly crowded 3', 6"-diphenyl-o-quaterphenyl (1) is one in which the interplanar angles of the pivot bonds between the 1, 2, 3-trisubstituted ring and three benzene rings are rather smaller than those of the less crowded 2'-phenyl-m-terphenyl (2).View full abstractDownload PDF (975K) -
KIYOFUMI FUKUKAWA, TOHRU UEDAO, TAKAO HIRANO1983 Volume 31 Issue 5 Pages 1582-1592
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNeplanocin A (1) and N6-benzoylneplanocin A (2) were converted to the corresponding 3', 6'-O-(tetraisopropyldisiloxane-1, 3-diyl)-neplanocin A's (3, 4). The 2'-hydroxy group in 3 and 4 was triflated (5, 6). Nucleophilic displacement of 5 and 6 with a number of nucleophiles (I-, Br-, Cl-, N3-, AcO-, AcS-) in hexamethylphosphoric triamide afforded the corresponding 2' (R)-substituted derivatives in high yields. The 2' (S)-azido derivatives were obtained in a similar manner from arabinoneplanocin A prepared by this method. Adenosine was also converted to 2' (R)-substituted derivatives, including arabinofuranosyladenine, as well as 2' (S)-substituted adenosines. The physical properties of these 2'-substituted derivatives of neplanocin A and adenosine, including nuclear magnetic resonance and circular dichroism spectra, are presented.View full abstractDownload PDF (1039K) -
MASAMI MORI, SETSUZO TEJIMA1983 Volume 31 Issue 5 Pages 1593-1600
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 6-Anhydro-2, 3, 3'-tri-O-benzyl-4', 6'-O-benzylidene-β-maltose (5), a maltose derivative having only one unprotected hydroxyl group at the C-2' position, was synthesized from 1, 6-anhydro-4', 6'-O-benzylidene-2'-O-tosyl-β-maltose (2) by benzylation followed by removal of the tosyl group with base. Compound 5 was converted into the corresponding ulose (7) by dimethylsulfoxide (DMSO)-Ac2O oxidation. Treatment of 7 with hydroxylamine gave the 2'-oxime (9). Reduction of 9 with LiAlH4 in ether and subsequent N-acetylation gave protected 1, 6-anhydro-β-N-acetyl-glucosaminylglucose (12) and -mannosaminylglucose (13) in a yield ratio of ca. 6 : 1. Debenzylidenation followed by debenzylation of 12 or 13 gave 1, 6-anhydro-β-N-acetyl-glucosaminylglucose (17) or-mannosaminylglucose (19). The title sugar was obtained was white prisms by acetolysis of the 1, 6-anhydro-β-linkage of peracetylated 17, followed by de-O-acetylation.View full abstractDownload PDF (868K) -
HIROKO YAMAGUCHI, YOSHIHIRO HARIGAYA, MASAYUKI ONDA1983 Volume 31 Issue 5 Pages 1601-1611
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of the photo-adduct (2) with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone under anhydrous conditions gives the imine (3) and the aniline (4). The oxidation of 2 in the presence of water and anhydrous methanol affords the 1-oxo-2β, 4β-epoxyimine (6) and the 4bα-methoxy-10bβ, 12β-epoxyimine (8), respectively. The mechanisms of formation of these compounds are discussed. The quinone (5), derived from 3 and 4, is reduced with sodium borohydride to yield the cis-diol (25) and the trans-diol (26). On reduction with lithium aluminum hydride and subsequent hydrogenation over palladiumcarbon, 8 gives the 4bβH-12β-anilino-10bβ-ol (33) and the 4bαH isomer (34).View full abstractDownload PDF (1103K) -
YOSHISUKE TSUDA, MD.ERAMUL HAQUE, KIMIHIRO YOSHIMOTO1983 Volume 31 Issue 5 Pages 1612-1624
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSelective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparison with the results of the (Bu3Sn)2-O method and direct benzoylation. The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group which bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group. The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.View full abstractDownload PDF (1157K) -
TAKUO OKUDA, YOSHIYUKI KIMURA, TAKASHI YOSHIDA, TSUTOMU HATANO, HIROMI ...1983 Volume 31 Issue 5 Pages 1625-1631
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inhibitory effects of 25 tannins and related compounds on the lipid peroxidation induced by adenine 5'-diphosphate (ADP) and ascorbic acid in rat liver mitochondria, and on that induced in rat liver microsomes by ADP and nicotinamide adenine dinucleotide phosphate (NADPH), were determined. All of the tannins, except for some polyphenols of low molecular weight and methylated polyphenols, showed significant inhibition in these two systems at the concentration of 1μg/ml. Almost complete inhibition of the lipid peroxidation in the two systems was shown by some ellagitannins such as pedunculagin, isoterchebin, etc., at the dose of 5μg/ml. Marked differences of the inhibitory activities were observed among the tannins depending on the tannin structure, including the stereoisomerism in the monomer of condensed tannin, and on the experimental system used. The inhibitory effects of most of the hydrolyzable tannins were higher than those of the condensed tannins in both systems. Some monomeric polyphenols, represented by (-)-epigallocatechin gallate, showed inhibitory effects stronger than those of the condensed tannins in these systems, particularly on the lipid peroxidation induced by ADP and NADPH. The inhibitory effects of these tannins in both systems were very much stronger than that of α-tocopherol.View full abstractDownload PDF (687K) -
YOSHIO ITOH, SETSUZO TEJIMA1983 Volume 31 Issue 5 Pages 1632-1640
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title trisaccharides (22 and 30) were synthesized by stepwise condensation of suitably protected monosaccharide units. 3-O-Allyl-2-O-benzoyl-4, 6-di-O-benzyl-α-D-glucopyranosyl bromide (9) and 2-acetamido-1, 6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (10) were coupled by a modified Koenigs-Knorr glycosidation to give the protected Glcβ1→4GlcNAc (12) in 63.7% yield. After removal of the benzoyl group of 12, the C-2' hydroxyl group was isomerized to the D-manno configuration by a sequence consisting of oxidation to ulose and stereoselective borohydride reduction to give the protected Manβ1→4GlcNAc (15). Benzylation of 15, followed by deallylation, gave the Manβ1→4GlcNAc derivative (18) having an unprotected hydroxyl group at the C-3' position. α-D-Mannosidation of 18 with acetobromomannose gave the protected Manα1→3Manβ1→4GlcNAc (20) in 47.1% yield. Deprotection of 20, followed by acetylation, yielded 22. 2-O-Acetyl-3, 4, 6-tri-O-benzyl-α-D-glucopyranosyl bromide (23) and 10 were coupled to give the protected Glcβ1→4GlcNAc (24) in 39.2% yield. Compound 30 was obtained from 24 via four steps using procedures analogous to those used to obtain 22 from 12.View full abstractDownload PDF (1092K) -
MASAHITO OCHIAI, TATSUZO UKITA, EIICHI FUJITA1983 Volume 31 Issue 5 Pages 1641-1645
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sex pheromones 1 and 2 of the red bollworm moth were synthesized in a highly stereoselective manner. The key step of their syntheses was the olefination reaction of E- and Z-allyl phenyl sulfones 8 and 12, affording the corresponding dienes 9 and 15, respectively.View full abstractDownload PDF (673K) -
TAMIO MORIKAWA, KENJI TSUJIHARA, MIKIO TAKEDA, YOSHIHISA ARAI1983 Volume 31 Issue 5 Pages 1646-1651
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of six 3-substituted 1-(2-chloroethyl)-3-(trans-2-hydroxycyclohexyl)-1-nitrosoureas (IVa-f) was prepared and tested for antitumor activities. Heating of cyclohexene oxide with various alkylamines followed by reaction with 2-chloroethyl isocyanate gave the corresponding ureas (IIIa-f), which were nitrosated with dinitrogen tetroxide to give the nitrosoureas (IVa-f). Decomposition of IVa and IV (IVd) d with aqueous sodium bicarbonate gave VIIa and VIIId, respectively, suggesting different modes activation. All the compounds obtained were remarkably active against leukemia L1210 and showed greater therapeutic ratios than the positive control : 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU). Against Ehrlich ascites tumor, the nitrosoureas (IVa-c) having one β-hydroxyl group on a cyclohexyl moiety exhibited rather weak activities, but the compounds (IVd-f) having two kinds of β-hydroxyl groups showed strong activities and large therapeutic ratios. This seems to be due to the difference in activation mode between these types of nitrosoureas.View full abstractDownload PDF (670K) -
GENICHIRO NONAKA, ITSUO NISHIOKA1983 Volume 31 Issue 5 Pages 1652-1658
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix tannin-related compounds (I-VI) have been isolated from commercial rhubarb, and their structures have been established on the basis of chemical and spectroscopic data to be 1-O-galloylglycerol (I), gallic acid 3-O-β-D-(6'-O-galloyl)-glucopyranoside (II), gallic acid 4-O-β-D-(6'-O-galloyl)-glucopyranoside (III), 1, 6-di-O-galloyl-β-D-glucose (IV), 6-O-galloylglucose (V) and 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2"-O-galloyl)-glucopyranoside (VI, named isolindleyin).View full abstractDownload PDF (753K) -
HIROSHI TAKAHASHI, YASUHIRO CHIDA, TSUTOMU SUZUKI, SAIZO YANAURA, YUJI ...1983 Volume 31 Issue 5 Pages 1659-1665
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(1S, 1'S)- and (1R, 1'R)-1-aryl-N-2'-hydroxy-1'-isopropylethyl-2-(4-substituted phenyl) ethylamines (7-13 and 18-23) were synthesized by the asymmetric reaction of (E)-(S)- and (E)-(R)-N-(2-hydroxy-1-isopropylethyl) arylmethylideneamines with Grignard reagents. The products showed 100% optical purities ; their absolute configurations were determined by means of circular dichroism. These optically pure chiral amines were converted into hydrochlorides and then evaluated for analgesic activity in the acetic acid-induced mouse-writhing assay. Among these compounds, the hydrochlorides of 9 (1S : 1'S, Ar=2-thienyl, R=H), 13 (1S : 1'S, Ar=2-thienyl, R=MeO), 19 (1R : 1'R, Ar=4-methoxyphenyl, R=H), 20 (1R : 1'R, Ar=2-thienyl, R=H), and 23 (1S : 1'S, Ar=2-thienyl, R=OH) showed inhibition of the writhing ; they were about equipotent with (-)-pentazocine hydrochloride. Moreover, the hydrochlorides of 8 (1S : 1'S, Ar=4-methoxyphenyl, R=H), 13 (1S : 1'S, Ar=2-thienyl, R=MeO), 18 (1R : 1'R, Ar=phenyl, R=H), 19 (1R : 1'R, Ar=4-methoxyphenyl, R=H), 20 (1R : 1'R, Ar=2-thienyl, R=H), and 21 (1R : 1'R, Ar=2-thienyl, R=MeO) were not antagonized by (-)-naloxone hydrochloride.View full abstractDownload PDF (757K) -
AKIRA KONO, SETSURO SUGATA, YASUHIRO HARA, MUTSUKO TANAKA, YOSHIHARU K ...1983 Volume 31 Issue 5 Pages 1666-1669
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive method for the assay of pyrimidine nucleoside phosphorylases in preparations of human and animal tissues by determination of pyrimidines is described. Pyrimidines formed enzymatically from thymidine, uridine, 5-fluorouridine, and 5'-deoxy-5-fluorouridine are determined by means of high-performance liquid chromatography with ultraviolet (UV) detection. The pyrimidines, after extraction with ethyl acetate, are separated by reversed-phase chromatography on μ-Bondapak C-18/Porasil. The limits of detection are 2.5, 1.0, and 2.0 pmol for thymine, uracil, and 5-fluorouracil, respectively.View full abstractDownload PDF (460K) -
MITSUKO ONITSUKA, MORIO FUJIU, NOBUO SHINMA, HIROMI B.MARUYAMA1983 Volume 31 Issue 5 Pages 1670-1675
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA potent inhibitor (Ro 09-0680) of rabbit platelet aggregation induced by collagen was isolated from a Chinese medicine, Tan-Shen, (radix of Salvia miltiorrhiza) and identified as a novel component, 2-isopropyl-8-methylphenanthrene-3, 4-dione (I). IC50 of I in the previously established assay was 6.6×10-6M, which is 30 times more potent than papaverine. Related diketophenanthrene derivatives such as tanshinone I, tanshinone II and cryptotanshinone were also found to have the inhibitory activity, though to lesser extents.View full abstractDownload PDF (633K) -
HIROKO KAWANO, KEI CHO, YASUYO HARUNA, YUICHI KAWAI, TADANORI MAYUMI, ...1983 Volume 31 Issue 5 Pages 1676-1681
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen ergothioneine was administered to rats for 7 d, the pentobarbital sleeping time was reduced significantly. This action was specific to ergothioneine and was not shown by various ergothioneine-related compounds (cysteine, glutathione, carnitine and histidine). This action of ergothioneine did not appear to be caused by induction of the drug-metabolizing enzyme system. The level of ergothioneine in the liver decreased markedly when phenobarbital or ethionine was administered to rats. Ergothioneine inhibited hepatic injury and significantly decreased the level of lipid peroxide induced by ethionine administration.View full abstractDownload PDF (653K) -
HIROKO KAWANO, HIROOMI MURATA, SADAFUMI IRIGUCHI, TADANORI MAYUMI, TAK ...1983 Volume 31 Issue 5 Pages 1682-1687
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSErgothioneine was examined in vitro for ability to inhibit lipid peroxide formation. Lipid peroxide formation in mouse liver homogenate was inhibited in a dose-related manner by 5-250 mM ergothioneine. Carnitine and histidine had no such effect. Even when lipid peroxide formation was enhanced by reduced nicotinamide adenine dinucleotide phosphate (NADPH) or ascorbic acid treatment, addition of 50 mM ergothioneine inhibited that formation by 50%. It was found that ergothioneine (1) remarkably enhanced glutathione peroxidase activity from liver cytosol, (2) increased the activity of mitochondrial Mn-superoxide dismutase, and (3) inhibited NADPH-cytochrome c reductase from rat liver microsomes. Thus, ergothioneine might be one of the heat-stable factors inhibiting lipid peroxide formation in the liver cytosol.View full abstractDownload PDF (641K) -
YOSHIHIRO MINAMI, KOUHEI YAZAWA, ZENZO TAMURA, TOSHIO TANAKA, TAKEHIKO ...1983 Volume 31 Issue 5 Pages 1688-1691
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIsogalactobiose (β-D-galactopyranosyl β-D-galactopyranoside), galsucrose (β-D-fructofuranosyl α-D-galactopyranoside) and lactosucrose (O-β-D-galactopyranosyl-(1→4)-O-α-D-glucopyranosyl β-D-fructofuranoside) were synthesized as potential sugar sources that selectively enhance the growth of bifidobacteria in the human intestines. Isogalactobiose was synthesized by means of the Koenigs-Knorr reaction and the others by using levansucrase. The structures of these sugars were confirmed by enzymic hydrolysis. All of the sugars synthesized were utilized by bifidobacteria, but not by strains of Lactobacillus acidophilus, Streptococcus faecalis and Escherichia coli. However, isogalactobiose was utilized by 65%, galsucrose by 62% and lactosucrose by 41% of thirty-seven strains of Enterobacteriaceae isolated from nineteen adults, while raffinose, which had seemed to be the best among commercially available sugars tested, was utilized by 49% of the strains.View full abstractDownload PDF (532K) -
AKIRA TAMURA, NAOKO MORIWAKI, TATSUZO FUJII1983 Volume 31 Issue 5 Pages 1692-1697
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAfter treatment of human erythrocytes at 37°C with a cationic amphiphilic drug (one of various tertiary amine phenothiazines, primaquine or n-decylamine), up to 45% of the membrane phosphatidylethanolamine (PE) was degraded by added phospholipase A2 from bee venom (untreated erythrocytes, 1-2%) and about 35% of the PE could be labelled by trinitrobenzenesulfonate (untreated erythrocytes, about 14%). Pancreatic phospholipase A2, which is virtually unable to hydrolyze the phospholipids of intact erythrocytes, degraded significant amounts of phosphatidylcholine and PE in the erythrocyte membrane pretreated with the above drugs. These results suggest that cationic drugs in general may alter the protein-lipid interaction of the membrane and thus release the inner layer phospholipid PE from possible locational restriction under the influence of certain proteins.View full abstractDownload PDF (714K) -
YOSHIKO SONODA, YOSHIHIRO SATO1983 Volume 31 Issue 5 Pages 1698-1701
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of oxygenated lanosterol derivatives (1-14) on cholesterol biosynthesis from [24-3H]-lanosterol were tested in 10000×g supernatant (S10) fraction of rat liver homogenate (RLH). Among the derivatives studied, 7-oxo-24, 25-dihydrolanosterol (11) was most active in depressing cholesterol biosynthesis from lanosterol. The inhibitory activities of these derivatives on cholesterol synthesis are discussed in relation to the position and stereochemistry of the oxygen group on the side chain and the sterol nucleus.View full abstractDownload PDF (416K) -
NORIKO MOTOHASHI, ITSUHIKO MORI1983 Volume 31 Issue 5 Pages 1702-1707
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn phosphate buffer (pH 6.8), reduced nicotinamide adenine dinucleotide (NADH) was oxidized by metmyoglobin or methemoglobin in the presence of Mn (II) ion and ergothioneine. The NADH oxidation was dependent on the concentrations of Mn (II) ion, ergothioneine and metmyoglobin (or methemoglobin). Various phosphorus compounds also influenced the oxidation. Orthophosphate was the most effective at concentrations or more than 50 mM. In contrast, nucleotides such as adenosine-5'-triphosphate (ATP), adenosine 5'-diphosphate (ADP) and adenosine-5'-monophosphate (AMP) were less effective. Superoxide dismutase or catalase inhibited the present NADH oxidation, suggesting the participation of superoxide anion (O-2) and H2O2 in this metmyoglobin system as well as the peroxidase system. Metmyoglobin pretreated with H2O2, i.e., ferrylmyoglobin, promoted the NADH oxidation reaction, but oxymyoglobin inhibited it. A mechanism is proposed for the oxidation of NADH by metmyoglobin or methemoglobin on the basis of the redox potential of ergothioneine, the formation of Mn-phosphate complex and the heme state of metmyoglobin or methemoglobin.View full abstractDownload PDF (618K) -
TERUO MURAKAMI, NOBORU YATA, AKIRA KAMADA1983 Volume 31 Issue 5 Pages 1708-1713
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of isoxazolyl-penicillins on the rectal absorption of ampicillin were investigated in rabbits and humans. The bioavailability of ampicillin following administration of a suppository in the presence or absence of an isoxazolyl-penicillin was determined from the blood level in rabbits and from the urinary excretion (0-6 h) in humans. Rectal absorption of ampicillin from the suppository was enhanced by the presence of an isoxazolyl-penicillin in both rabbits and humans, though the effect was much greater in rabbits than in humans. The absorption-promoting effects of isoxazolyl-penicillins appeared to be related to their partition coefficients between n-octanol and buffer solution (pH 7.4).View full abstractDownload PDF (619K) -
HISAYUKI TANIZAWA, YASUYUKI SAZUKA, YOSHIO TAKINO1983 Volume 31 Issue 5 Pages 1714-1718
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of adriamycin (ADR), an anthracycline antitumor antibiotic, on lipid peroxide levels in tissues of male CDF1 strain mice was investigated by using thiobarbituric acid fluorophotometry, as reported in a previous paper (Tanizawa et al., Chem. Pharm. Bull., 29, 2910 (1980)). The body weight of mice decreased markedly after intraperitoneal injection of ADR at a dose of 15 mg/kg. The loss reached 25% of the initial weight on the 6th day. The relative weight of organs such as the heart, liver, kidney and spleen also decreased, with a minimum on the 4th day. In contrasts, the lipid peroxide levels in the heart, liver, kidney and spleen increased rapidly, reaching a peak on the 4th day. The lipid peroxide level in the heart increased by 2.6-fold on the 4th day and the level was maintained, despite subsequent decreases in the liver and kidney. No increase of lipid peroxide levels in the serum and lung was observed after ADR injection in mice. ADR had a greater lipid peroxide-increasing effect in mice than daunomycin at the same dose.View full abstractDownload PDF (567K) -
KAZUMI TAKEYA, MASATAKA ITOIGAWA, HIROSHI FURUKAWA1983 Volume 31 Issue 5 Pages 1719-1725
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHelenalin, a pseudoguaianolide sesquiterpene lactone which has hitherto been known as a potent antitumor and cytotoxic substance was found in this study to have a positive inotropic effect (PIE) on the myocardium. Left atrial strips and papillary muscles isolated from the guinea-pig heart were driven at a frequency of 1.0 Hz in Krebs-Henseleit solution at 30°C. Helenalin produced an increase in the force of contraction (Fc) depending on its concentration in the range between 10-5-10-3M. The potency of helenalin, expressed as pD2 value, was 4.69 and 4.11 in the left atria and papillary muscle, respectively. The PIE of 3×10-4M helenalin was equivalent to 78% of that of 10-5M norepinephrine. The PIE of a higher concentration of helenalin (above 3×10-4M) was neither affected by reserpinization nor by propranolol (3×10-5M), but the PIE at lower concentrations was inhibited by reserpinization or propranolol. We conclude that the PIE of helenalin is produced in two different ways ; one is catecholamine-mediated and the other is an unknown direct effect.View full abstractDownload PDF (687K) -
HIROSHI YOSHIKAWA, SHOZO MURANISHI, NAOKO SUGIHIRA, HITOSHI SEZAKI1983 Volume 31 Issue 5 Pages 1726-1732
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of lymphatic transfer of bleomycin from the lumen of the small intestine of rats following the administration of a bifunctional delivery system was investigated. This system is a combination of macromolecular bleomycin·dextran sulfate complex as a lymphotropic carrier and lipid-surfactant mixed micelles as an absorption promoter. After administration of this bifunctional delivery system into the lumen of the small intestine, 56% of the complex was left intact in the lumen after 2 h, but 85, 95 and 97% of the absorbed bleomycin were detected as the free drug in the tissue of the small intestine, the lymph and the blood, respectively. The absorption percentage of bleomycin from the lumen of the small intestine at 3 h after the administration of the bifunctional delivery system was significantly different from that of dextran sulfate, and the total lymphatic transfer of dextran sulfate was greater than that of bleomycin. These findings suggest that the extent of the selective lymphatic transfer of bleomycin was smaller than that of dextran sulfate because of the dissociation of the bleomycin·dextran sulfate complex in the lumen and the tissue of the small intestine.View full abstractDownload PDF (783K) -
MASATOSHI YAMATO, YASUO TAKEUCHI, KUNIKO HASHIGAKI, KYOKO HATTORI, EIK ...1983 Volume 31 Issue 5 Pages 1733-1737
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral methods for the preparations of 3-substituted benzoxazoline-2-thiones (1) were examined. Method B via the thiation of 3-substituted benzoxazolin-2-one (5) with phosphorus pentasulfide was found to be applicable to the preparation of most analogs of 1, with a few exceptions. Method C via the cyclization of 2-(alkylamino) phenol (7) with potassium O-methyldithiocarbonate was suitable for the preparation of analogs with a group sensitive to high temperature or with an aryl-(including aromatic heterocyclic ring) methyl group. In addition, the reaction of benzoxazoline-2-thione (2) with acetals such as 1-ethoxy-isochroman, 2-ethoxytetrahydrofuran, and 2-ethoxytetrahydropyran, or with Michael acceptors such as 2, 3-dihydrofuran and 2H-3, 4-dihydropyran, gave 3-substituted benzoxazoline-2-thione (1d-f).View full abstractDownload PDF (588K) -
SHOZO KAMIYA, SHOKO SUEYOSHI1983 Volume 31 Issue 5 Pages 1738-1742
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNitrosation of 1-methyl-(Ia), 1-(2-chloroethyl)-(Ib) and 1-phenyl-3-(2-pyridylmethyl)-urea (Id) with hydrochloric acid and sodium nitrite gave exclusively the corresponding 1-nitrosoureas (IIa, b, d). However, nitrosation of the 1-isopropylurea (Ic) gave a mixture of the 1-nitrosourea (IIc) and the 3-nitrosourea (IIIc). Similar results were also obtained in the nitrosation of 1-substituted 3-(2-pyridylethyl) ureas (Ie-h). The reaction of the nitrosoureas and m-chloroperbenzoic acid in chloroform gave the N-oxides (IVa-f, Vc, f, g), which were more stable than the nitrosoureas.View full abstractDownload PDF (670K) -
HIDEJI ITOKAWA, HAJIME MATSUMOTO, SUSUMU MIHASHI1983 Volume 31 Issue 5 Pages 1743-1745
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHumulene (I), (-)-germacrene-D (II), and (-)-germacra-4 (15), 5 (E), 10 (14)-trien-1β-ol (III) were isolated from the fruits of Torilis japonica. the latter two compounds (II and III) were determined to have optical purities of about 40 and 30%, respectively.View full abstractDownload PDF (424K) -
JUN ADACHI, HIDENOBU TAKAHATA, KEIICHI NOMURA, KATSUTADA MASUDA1983 Volume 31 Issue 5 Pages 1746-1750
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew mesoionic heterocycles, 3-aryl- and 3-alkyl-1, 2, 3-thiadiazolium-4-thiolates (4 and 8), were synthesized by two different procedures. Some of the S-methyl derivatives of these compounds gave the corresponding mesoionic 4-olate derivatives on alkaline hydrolysis.View full abstractDownload PDF (614K) -
YUJI SUZUKI, HIROSHI TAKAHASHI1983 Volume 31 Issue 5 Pages 1751-1753
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSalicylaldehydes with electron-withdrawing groups, i.e., 2-hydroxy-5-nitrobenzaldehyde (2a), methyl 3-formyl-4-hydroxybenzoate (2b), methyl 5-chloro-3-formyl-2-hydroxybenzoate (2c), 3, 5-dichloro-2-hydroxybenzaldehyde (2d), 5-cyano-2-hydroxybenzaldehyde (2e), and 5-fluoro-2-hydroxybenzaldehyde (2f), were synthesized by the formylation of the corresponding phenols (1a-f) with hexamethylenetetramine in 75% polyphosphoric acid, methanesulfonic acid, or trifluoroacetic acid. The yields of these reactions were better than those of the Duff reaction.View full abstractDownload PDF (400K) -
TAKAO MORI, HIDEO BANDO, YOSHIO KANAIWA, TAKASHI AMIYA, KAZUYA KURATA1983 Volume 31 Issue 5 Pages 1754-1756
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBis (2, 3, 6-tibromo-4, 5-dimethoxybenzyl) ether (IV), 2, 3, 6-tribromo-4, 5-dimethoxybenzyl methyl ether (V), 2, 3, 6-tribromo-4, 5-dimethoxybenzyl ethyl ether (VI) and 2, 3, 6-tribromo-4, 5-dimethoxybenzyl alcohol (VIII) were prepared by simple procedures involving one-step bromination from 3, 4-dimethoxybenzylacetate (IX).View full abstractDownload PDF (389K) -
HAJIMU YAMAMOTO, IKUKATSU SUZUKI, AKIRA MIZUTANI1983 Volume 31 Issue 5 Pages 1757-1760
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of P-MSY, a hypocalcemic protein from bovine parotid gland, on the levels of cyclic adenosine-5'-monophosphate (cAMP) and cyclic guanosine-5'-monophosphosphate (cGMP) in thymic and splenic cells of 4-week-old C57BL/6 mice was studied in vitro. Preliminary studies on the effect of 0.5mg/ml of P-MSY indicated that an incubation time of 10 min gave the maximum response. This incubation time was used in dose-response studies. In thymic cells, the increase of cAMP content was dose-dependent (2-3.6 fold increase in response to 1 mg/ml P-MSY), but little change of cGMP was observed. The ratio of cAMP/cGMP increased about 1.7-2.5 times at a concentration of 0.2 mg/ml P-MSY. cAMP did not increase as much in the splenic cells as in the thymic cells. The difference between the thymus and spleen in response to P-MSY is probably due to the relatively greater influence of P-MSY on T-cells of the thymus.View full abstractDownload PDF (506K) -
MAKIKO SUZUKI, MITSUO WATANABE1983 Volume 31 Issue 5 Pages 1761-1764
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAfter intravenous injection of tryptophan-U-14C into mice, the radioactivities of carcinogenic tryptophan metabolites in the organs were determined. Kynurenine, 3-hydroxykynurenine, 3-hydroxyanthranilic acid and xanthurenic acid in the liver, pancreas, kidneys and bladder were separated by thin layer chromatography and the radioactivity of each metabolite was counted. The radioactivities of xanthurenic acid were 25-80, 50-115, 200-480 and 170-370 nCi/g in the pancreas, liver, kidneys and bladder, respectively. The radioactivities were in the order xanthurenic acid>kynurenine>3-hydroxykynurenine and 3-hydroxyanthranilic acid in every organ. The radioactivity of xanthurenic acid was especially high in the kidneys and bladder.View full abstractDownload PDF (448K) -
YOSHIHIRO SATO, YOSHIKO SONODA, MASUO MORISAKI, NOBUO IKEKAWA1983 Volume 31 Issue 5 Pages 1765-1767
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCholesterol biosynthesis was examined with rat hepatic subcellular 10000×g supernatant fraction incubated with [24-3H]-lanosterol in the presence of one of twelve cholesterol analogs (1-12) including sitosterol. Cholesterol analogs (40μM) with different sizes of side chains exhibited very minor inhibitory effects (2-7%) compared with that of cholesterol (21%) on the synthesis of cholesterol from [24-3H]-lanosterol (18μM). The structure-inhibitory activity relationship of cholesterol analogs is discussed.View full abstractDownload PDF (356K) -
YORISHIGE IMAMURA, HIROYUKI MORI, HISASHI ICHIBAGASE1983 Volume 31 Issue 5 Pages 1768-1771
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo groups of rabbits categorized on the basis of their acetylation capacity were used in this study as fast and slow acetylator rabbits. The ratio of the unbound fraction of sulfadimethoxine (SDM) in plasma at 2 h after intravenous bolus injection of SDM in combination with probenecid to the unbound fraction of SDM in plasma at 2 h after intravenous bolus injection of SDM alone was determined in fast and slow acetylator rabbits. A significant difference in the ratio of unbound fraction of SDM was observed between fast and slow acetylator rabbits. This indicates that the effect of probenecid on the in vivo binding of SDM to plasma proteins is dependent on the acetylation capacity for SDM in rabbits. In addition, probenecid was found to cause a significant decrease in the plasma concentration of SDM in fast acetylator rabbits, but caused no significant change in the plasma concentration of SDM in slow acetylator rabbits.View full abstractDownload PDF (456K) -
TSUTAO KURECHI, TETSUTA KATO1983 Volume 31 Issue 5 Pages 1772-1776
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydrogen donation from butylated hydroxyanisole (BHA) and/or butylated hydroxytoluene (BHT) to the peroxyl radical prepared by cobalt-catalyzed cleavage of tert-butylhydroperoxide was investigated, and the relation of this process to synergism in the antioxidative effect was discussed. BHA initially donated a hydrogen to the peroxyl radical to form its phenoxyl radical, and this radical reacted with either the peroxyl radical or another phenoxyl radical to form o-benzoquinone or the dimer. BHT reacted with the peroxyl radical to form its adduct. In the combination of BHA and BHT, BHA donated a hydrogen to the peroxyl radical initially, and its phenoxyl radical accepted hydrogen from BHT to regenerate BHA, with enhanced oxidation of BHT to quinone methide. This hydrogen acceptance of the phenoxyl radical of BHA from BHT may be closely correlated with the synergism in the antioxidative effect of the mixture of BHA and BHT.View full abstractDownload PDF (592K) -
Isamu Murakoshi, Chiharu Koide, Fumio Ikegami, Kikuko NASU1983 Volume 31 Issue 5 Pages 1777-1779
Published: May 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-(6-Benzylaminopurin-9-yl) alanine (3), a metabolite of the cytokinin 6-benzylaminopurine (2), was confirmed to be derived from O-acetyl-L-serine (1) and 2 by an enzyme in higher plants. Some properties of the enzyme are described.View full abstractDownload PDF (378K)