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Volume 29, Issue 12
Displaying 1-50 of 55 articles from this issue
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YOKO MIYAMOTO, TOSHIMASA ISHIDA, MASATOSHI INOUE1981 Volume 29 Issue 12 Pages 3427-3432
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a model study of the intramolecular interaction between the adenine and pyridinium rings of nicotinamide adenine dinucleotide (NAD+), conformational analysis of 1-[3-(adenin-9-yl) propyl]-3-carbamoylpyridinium cation was carried out by means of semiempirical energy calculation. The extended conformation of the molecule, which was observed in the crystal structure, was found to be energetically a metastable one. The most energetically stable conformations seem to be folded forms, especially forms in which the two aromatic rings are stacked ; four kinds of stacking modes were observed.View full abstractDownload PDF (607K) -
TOSHIHIRO YAMADA, YOUICHI NOBUHARA, HIROSHI SHIMAMURA, KAZUO YOSHIHARA ...1981 Volume 29 Issue 12 Pages 3433-3439
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pyridine ring of 2-phenyl-2-(2-pyridyl) thioacetamide (Ia), the lead compound for the present study, was replaced by a pyridazine ring in the hope of obtaining more potent and less toxic drugs with long-lasting action, and a series of 2-phenyl-2-(3-pyridazinyl) thioacetamide derivatives (II) was synthesized from halopyridazines (III) and phenyl-acetonitriles via the key intermediates, 2-phenyl-2-(3-pyridazinyl) acetonitrile derivatives (IV). The chemical structure of II appears to be in equilibrium between the pyridazine form and the pyridazinone-methide form on the basis of nuclear magnetic resonance (NMR) and ultraviolet (UV) spectral data. The antisecretory activity and acute toxicity of II were investigated and the structure-activity relationships are discussed. Among the compounds tested, 2-Phenyl-2-(3-pyridazinyl) thioacetamide (IIa) and 2-(6-methyl-3-pyridazinyl)-2-phenylthioacetamide (IIb) possessed long-lasting, potent activity when administered to rats at 20 mg/kg. The acute toxicities of IIa and IIb were about half to one-third of that of Ia in mice.View full abstractDownload PDF (647K) -
EIKO OHTSUKA, SUSUMU SHIBAHARA, MORIO IKEHARA1981 Volume 29 Issue 12 Pages 3440-3448
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSp-Chlorophenyl N-(p-methoxyphenyl) chlorophosphoramidate was used to phosphorylate the 3'-hydroxyl groups of N, 5'-O-protected deoxyribonucleosides. These nucleotides served as the 3'-terminal unit in the synthesis of fully protected oligonucleotides, and the p-anisidine was readily removed by treatment with isoamyl nitrite to generate the 3'-phosphodiester for condensations. This approach was suitable for complete purification of fully protected oligonucleotides by chromatography, which was essential to obtain products. Deoxyoligonucleotides complementary to the anticodon loop of E. coli tRNAMetf were synthesized by condensation of di-, tri- and tetranucleotide blocks (dATp, dTATp and dTTATp) with protected dGAG. The products (dA-T-G-A-G, d-T-A-T-G-A-G and d-T-T-A-T-G-A-G) were isolated by anion-exchange or reverse phase high pressure liquid chromatography.View full abstractDownload PDF (862K) -
MASAKO MURAOKA1981 Volume 29 Issue 12 Pages 3449-3454
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 6-Diamino-9-β-D-ribofuranosylpurine (I) was brominated with saturated bromine-water to the 8-bromo compound (II), which was tosylated at the 2'-hydroxygroup via the 2', 3'-O-dibutylstannylene compound (III). The resulting 2, 6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribofuranosyl)-purine (IV) was cyclized with thiourea in n-propanol or 40% sodium hydrogen sulfide to give 2, 6-diamino-8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosylpurine (V) in yields of 40% and 80%, respectively. Alternatively, 8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosylguanine (VI) was acetylated and chlorinated with phosphoryl chloride to give the 2-amino-6-chloropurine-8, 2'-S-cyclonucleoside derivative (VIII), which was aminated with ammonia in methanol to afford the 2, 6-diaminopurine cyclonucleoside (V) in a yield of 45%. Catalytic desulfurization of the cyclonucleoside (V) gave 2, 6-diamino-9-(2'-deoxy-β-D-ribofuranosyl)-purine (IX). Some physical properties of these compounds were elucidated by ultraviolet (UV), nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopy. The CD spectra of these nucleosides and cyclonucleoside were similar to those of the corresponding adenine nucleosides and cyclonucleoside in general.View full abstractDownload PDF (722K) -
NOBUTOSHI TANAKA, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMING CHEN, LUIS ...1981 Volume 29 Issue 12 Pages 3455-3463
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe constituents of five Costa Rican ferns of Preridaceae were investigated. The ferns and isolated compounds are as follows. Acrostichum aureum : quercetin 3-O-β-D-glucoside (I), ponasterone A (III). Neurocallis praestantissima : 2-deoxy-D-glucose (IV), 3, 6-anhydro-2-deoxy-D-glucose (V). Pteris podophylla : 6-(2-chloroethyl)-2 (S)-hydroxy-methyl-5, 7-dimethylindan-1-one (X), pterosin G (XI), kaempferol 3, 7-di-O-α-L-rhamnoside (II), apigenin 7-O-β-D-glucoside (VI), luteolin 7-O-β-D-glucoside (VII). Pteris livida : pterosin C (VIII), pterosin S (IX), 9-hydroxy-15-oxo-ent-kaur-16-en-19-oyl-β-D-glucoside (XII), 6β, 11β-dihydroxy-15-oxo-ent-kaur-16-en-19-oyl-β-D-glucoside (XIII), 6β, 9-dihydroxy-15-oxo-ent-kaur-16-en-19-oyl-β-D-glucoside (XIV), paniculoside III (XV), ptero-kaurene L1 (XVI), 11β-hydroxy-15-oxo-ent-kaur-16-en-19-oic acid (XIX). Pteris altissima : VII, XI, XII, XIII, XV. Among the above products, X, XII, XIII and XIV are new compounds and their structures were elucidated by chemical and physicochemical methods.View full abstractDownload PDF (1038K) -
TOSHIO YONETA, TOMIO MATSUNO, SHUNZO FUKATSU1981 Volume 29 Issue 12 Pages 3464-3468
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new deoxygenation of kanamycin A leading to 3', 4'-dideoxykanamycin A and 4'-deoxykanamycin A is described. The key stage in the syntheses involves the formation of the 3', 4'-anhydro-4'-epi derivative (5) followed by its conversion to the 3'Δ and 4'-deoxy derivative through the iodohydrin. Compound 5 was prepared by the treatment of 2', 3', 2"-tri-O-benzoyl-4", 6"-O-cyclohexylidene-4'-O-methylsulfonyl-tetra-N-tert-butyloxycar-bonylkanamycin A (4) with sodium methoxide.View full abstractDownload PDF (586K) -
TOSHIO YONETA, TOMIO MATSUNO, HIDETAKA NANAHOSHI, SHUNZO FUKATSU1981 Volume 29 Issue 12 Pages 3469-3473
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new synthetic route has been exploited for the large-scale production of 3'-deoxykanamycin A. The key stage in the synthesis involves the formation of the 3', 4'-anhydro-3'-epi derivative (9) or 2', 3'-anhydro-3'-epi derivative (10) followed by conversion to the 3'-deoxy derivative by reduction with Raney-nickel or sodium borohydride. Compound (9) or (10) was prepared by the treatment of 2', 2"-di-O-benzoyl-3'-O-methylsulfonyl-tetra-N-ethoxycarbonylkanamycin A with sodium methoxide.View full abstractDownload PDF (567K) -
(±)-3β, 6β-Dihydroxy-10βHfuranoeremophilan-9-one, and (±)-3β, 6β-Dihydroxy-10αH-furanoeremophilan-9-oneKOJI YAMAKAWA, TSUYOSHI SATOH1981 Volume 29 Issue 12 Pages 3474-3485
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe total syntheses of several highly oxygenated, 1, 10-dehydrofuranoeremophilanes [(±)-6β-hydroxy-1, 10-dehydrofuranoeremophilan-9-one (1a), (±)-decompositin (1b), (±)-dihydrodecompositin (3), (±)-adenostylone (1c), (±)-3β, 6β-dipropionyleuryopsin-9-one (2b)] and polyoxy compounds [(±)-3β, 6β-dihydroxy-10βH-furanoeremophilan-9-one (4), (±)-3β, 6β-dihydroxy-10αH-furanoeremophilan-9-one (5), and 3β-acetoxy-6β-isobutyroxy-furanoeremophilan-9-one (28b)] from a bicyclic enone (6a) are described. Treatment of 10α-hydroxy-6, 9-dioxo compounds (8a, 18 and 23) with SOCl2-pyridine gave the corresponding 1, 10-dehydro-6, 9-dioxo compounds (11, 20 and 24, respectively). NaBH4 reduction of 11, 20 and 24 afforded the 6β-hydroxy derivatives (12a, 1a and 2a, respectively) regio- and stereoselectively. (±)-1a was converted into (±)-1b, (±)-1c, and (±)-3. (±)-2a was also converted into (±)-2b. Catalytic reduction of 12a with H2/Pd gave the 10α-H and 10β-H compounds (25 and 26a). Deketalization of 25 and 26a with aq. AcOH followed by reduction with NaBH4 gave (±)-5 and (±)-4, respectively. Esterification of 26a with 2-methylbutyric anhydride-pyridine gave the ester (26b), which was converted to (±)-28a and 28b.View full abstractDownload PDF (1320K) -
KOOHEI NOZAWA, MIKIKO YAMADA, YOSHIKO TSUDA, KENICHI KAWAI, SHOICHI NA ...1981 Volume 29 Issue 12 Pages 3486-3493
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious cis- and trans-3-aryl-3, 4-dihydro-8-(hydroxy or methoxy) isocoumarin-4-carboxylic acids (3-16) and their methyl esters (21-29) were prepared. In addition, cis- and trans-3, 4-dihydro-8-(hydroxy or methoxy)-4-hydroxyacetyl-3-phenylisocoumarins (33 or 32, and 35 or 34), cis- and trans-4-diazoacetyl-3, 4-dihydro-8-methoxy-3-phenylisocoumarins (30 and 31), trans-4-acetoxyacetyl-3, 4-dihydro-8-methoxy-3-phenylisocoumarin (36), and trans-4-acetyl-3, 4-dihydro-8-(hydroxy or methoxy)-3-phenylisocoumarins (38 or 37) were prepared. All the 3, 4-dihydroisocoumarins thus prepared were examined in vitro for antifungal activity. The introduction of a carboxyl, carbomethoxy, acetyl, diazoacetyl or hydroxyacetyl group at the 4-position of the 3, 4-dihydroisocoumarin nucleus resulted in the disappearance of the activity.View full abstractDownload PDF (832K) -
MASATOSHI YAMATO, KUNIKO HASHIGAKI, AKIRA TSUTSUMI, KENJI TASAKA1981 Volume 29 Issue 12 Pages 3494-3498
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructural modification of the isocoumarin moiety (A and B rings) of 1'-benzylspiro-[isocoumarin-piperidines] (1a and 2a), which inhibit the compound 48/80-induced release of histamine from isolated rat peritoneal mast cells, was undertaken to clarify the structure-activity relationship. Chromanone (3), chroman (4), 1, 3-benzoxazine (5), 1, 3-benzothiazine (6), and 4-quinazolinone (7) analogs were active, although there were differences in potency. Substituent effects on the benzene moiety (A ring) of 3 were examined.View full abstractDownload PDF (606K) -
TAKAO KANEKO, MITSUYOSHI MATSUO, YOICHI IITAKA1981 Volume 29 Issue 12 Pages 3499-3506
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen indole reacted with titanium (III)- or iron (II)-hydrogen peroxide systems, the products varied widely, depending on the pH of the reaction solutions. Under acidic conditions, indole gave rise to oxindole, 2, 3'-biindole and a novel indole trimer, diindolo-[2, 3-a : 2', 3'-c] carbazole. Under neutral conditions, indole was converted to oxindole, hydroxyindoles and 3, 3'-biindole. The structure of the trimer was determined by X-ray diffraction analysis of its monoacetyl derivative. A possible mechanism for the formation of the products is proposed.View full abstractDownload PDF (816K) -
NOBUYUKI OKAMURA, AKIRA YAGI, ITSUO NISHIOKA1981 Volume 29 Issue 12 Pages 3507-3514
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew glycosides, zizybeoside I (I) and II (II), zizyvoside I (IV) and II (V), and a mixture of 6, 8-di-C-glucosyl-2 (S)-naringenin and 6, 8-di-C-glucosyl-2 (R)-naringenin (compound A), together with vomifoliol and roseoside, were isolated from the ethanol extract of Zizyphi Fructus. On the basis of spectral and chemical evidence the structures of the new glycosides were determined as benzyl β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (I), benzyl β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (II), vomifoliol 9-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (IV), vomifoliol 9-O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranoside (V), 6, 8-di-C-glucosyl-2 (S)-naringenin (VII) and 6, 8-di-C-glucosyl-2 (R)-naringenin (VIII).View full abstractDownload PDF (941K) -
HIROAKI TAGAWA, SHIRO KUBO, FUMIYOSHI ISHIKAWA1981 Volume 29 Issue 12 Pages 3515-3521
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a search for new antiinflammatory agents, some new tricyclic compounds and their acetic acid derivatives were prepared. Pyrido [2, 3-c] [1] benzoxepin-5 (11H)-one (4a) and pyrido [3, 2-c] [1] benzoxepin-11 (5H)-one (10a) and their thiepin analogs (4b, 10b) were synthesized by cyclization of the corresponding pyridinecarboxylic acid derivatives (3a, 3b, 9a and 9b) with polyphosphoric acid (PPA). The acetic acid derivatives (12a-b) of 4a-b were prepared via methyl derivatives (14a-b) of 4a-b. Their antiinflammatory activities were less potent than those of the corresponding dibenz [b, e] oxepin- and dibenz-[b, e] thiepinacetic acids.View full abstractDownload PDF (700K) -
TAISEI UEDA, HIDESHI MASE, NORIICHI ODA, ISOO ITO1981 Volume 29 Issue 12 Pages 3522-3528
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses of pyrano [2, 3-c] pyrazoles by means of the reaction of 3-ethoxycarbonyl-5-hydroxy-1-methyl (or phenyl) pyrazole (Ia, b) and acetylenecarboxylates or ethyl acetoacetate were examined. The reactions of Ia, b with acetylenecarboxylates gave 3-ethoxycarbonyl-4-substituted-1-methyl (or phenyl) pyrano [2, 3-c] pyrazol-6 (1H)-ones (IIa-c) in 5.9-23.9% yields. The Pechmann-Duisberg reaction of Ia-c with ethyl acetoacetate gave 3-ethoxycarbonyl-4-methyl-1-substitutedpyrano [2, 3-c] pyrazol-6 (1H)-ones (VIIa-c) in 33.1-46.2% yields. Similar reactions of 5-hydroxy-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrazoles (IXa, b) with ethyl acetoacetate gave 4-methyl-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrano [2, 3-c] pyrazol-6 (1H)-ones (Xa, b) in 17.4-30% yields. The newly synthesized pyrano [2, 3-c] pyrazoles (Xa, Xb, XII) showed analgesic activity in mice when tested by two methods.View full abstractDownload PDF (772K) -
RYUJI TACHIKAWA, KAZUYUKI WACHI, SADAO SATO, ATSUSUKE TERADA1981 Volume 29 Issue 12 Pages 3529-3535
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel S-N bond formation through 3, 3-sigmatropic rearrangement in the reaction of imidoyl chlorides of 1, 3-benzoxazines (1) with 2-mercaptopyridine N-oxide (8) is described. Treatment of the imidoyl chlorides (1a-f) with 2-hydroxypyridine N-oxide (2) afforded the corresponding pyridone derivatives (3a-f). When 2-mercaptopyridine N-oxide (8) was used instead of 2, the thiopyridones (7) or N-oxides (9) were obtained and both compounds were transformed to 3-(2-pyridylthio)-4-oxo-2, 3-dihydro-1, 3-benzoxazines (13) through electrocyclic rearrangement on heating in a suitable solvent.View full abstractDownload PDF (701K) -
USHIO SANKAWA, HISAO SHIMADA, TOSHITSUGU SATO, TAKESHI KINOSHITA, KAZU ...1981 Volume 29 Issue 12 Pages 3536-3542
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe biosynthesis of scytalone, a simple derivative of tetralone, has been studied by using [1, 2-13C2] and [2-13C, 2-2H3]-acetate. Scytalone labelled by [1, 2-13C2]-acetate showed an unusual coupling pattern in the 13C-nuclear magnetic resonance (NMR) spectrum, indicating that all the carbon atoms coupled to both of the adjacent carbons. The results clearly demonstrate that scytalone is biosynthesized via a symmetrical aromatic intermediate, 1, 3, 6, 8-tetrahydroxynaphthalene. Incorporation of 2H into C-4 and -5 from [2-13C, 2-2H3]-acetate was demonstrated by 1H and 2H decoupled 13C-NMR. In contrast, 2H was not observed on the other potential sites of labelling, C-2 and C-7. It has been shown that the use of [2-13C, 2-2H3]-acetate is effective in tracing the fate of acetate hydrogen in polyketide biosynthesis.View full abstractDownload PDF (686K) -
HIROSHI YAMANAKA, MASAFUMI SHIRAIWA, ETSUKO YAMAMOTO, TAKAO SAKAMOTO1981 Volume 29 Issue 12 Pages 3543-3547
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3, 5-Dimethyl-4-iodoisoxazole (1a) reacted with phenylacetylene with catalysis by palladium (II) chloride-triphenylphosphine complex to give 3, 5-dimethyl-4-phenylethynyl-isoxazole (2a). When 1a was treated with styrene under similar conditions, 3, 5-dimethyl-4-trans-styrylisoxazole (3a) was obtained. In contrast, the palladium-catalyzed crosscoupling reaction of 3-phenyl-5-bromoisoxazole (4) with styrene afforded 3, 3'-diphenyl-5, 5'-biisoxazole (6) as the main product, instead of the desired styryl compound (5a). However, 3-phenyl-5-phenylethynylisoxazole (7a) was obtained, as in the case of 1a, by the reaction of 4 with phenylacetylene. Some additional examples of these coupling reactions are also described.View full abstractDownload PDF (647K) -
HIROSHI YAMANAKA, MASAFUMI SHIRAIWA, TAKAO SAKAMOTO, SHOETSU KONNO1981 Volume 29 Issue 12 Pages 3548-3553
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydration of 5-isoxazolyl-phenyl (or -butyl) acetylenes (1a, b) in dilute sulfuric acid in the presence of mercuric sulfate afforded 5-isoxazolylmethyl phenyl (or butyl) ketones (3a, b), predominantly. In contrast, the hydration of 4-isoxazolyl-phenyl (or -butyl)-acetylenes (2a-d) under identical conditions gave 4-isoxazolyl benzyl (or pentyl) ketones (5a-d) as the main products. The structure of one of these products, 3, 5-dimethyl-4-isoxazolyl benzyl ketone (5a), was determined by Beckmann rearrangement. Isoxazoles containing a cis-alkene or alkane chain were obtained by the catalytic reduction of the above acetylenes without cleaving the isoxazole nucleus.View full abstractDownload PDF (714K) -
SHOETSU KONNO, MASAFUMI SHIRAIWA, HIROSHI YAMANAKA1981 Volume 29 Issue 12 Pages 3554-3560
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudies were carried out on the hydration and hydrogenation of the triple bond in quinoline and isoquinoline derivatives containing an ethynyl substituent linked directly to the pyridine moiety. Fourteen kinds of ethynyl quinolines and isoquinolines such as 2-, 3-, 4-phenylethynylquinoline, 2-, 3-, 4-(1-hexynyl) quinoline, 2-(1-propynyl) quinoline, 1-, 3-, 4-phenylethynylisoquinoline, 1-, 3-, 4-(1-hexynyl) isoquinoline, and 1-(1-propynyl)-isoquinoline were converted into the corresponding acylmethyl derivatives with high selectivity, when they were heated in dilute sulfuric acid in the presence of mercuric sulfate. In all cases, no products due to reverse hydration were isolated. Partial catalytic reduction of the ethynyl linkage of the above compounds is possible, while exhaustive reduction afforded quinolines and isoquinolines with a saturated side chain.View full abstractDownload PDF (731K) -
TOSHIO MIYASE, HIROKO KAWASAKI, TADATAKA NORO, AKIRA UENO, SEIGO FUKUS ...1981 Volume 29 Issue 12 Pages 3561-3564
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new furanoid diterpenes, teucjaponin A (II) and teucjaponin B (V), have been isolated from Teucrium japonicum HOUTT. together with teucvin (I) and their structures were determined on the basis of chemical and spectral data. Teucjaponin A showed antifeedant activity for Prodenia litura.View full abstractDownload PDF (487K) -
HIROMICHI TANAKA, HIROYUKI HAYAKAWA, TADASHI MIYASAKA1981 Volume 29 Issue 12 Pages 3565-3572
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Aroyluridines, a hitherto unknown class of uridine derivatives, were synthesized from 2', 3'-O-isopropylidene-5'-O-methoxymethyluridine via regiospecific lithiation.View full abstractDownload PDF (912K) -
SEIICHI UESUGI, TOSHIO SHIDA, MORIO IKEHARA1981 Volume 29 Issue 12 Pages 3573-3585
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo elucidate the conformational properties and their chain length dependency in solution of oligodeoxyribonucleotides containing an alternating C-G sequence, which have been shown to take a left-handed duplex structure in crystals, d (C-G), d (C-G-C-G) and d (C-G-C-G-C-G) were synthesized by a modified triester method and characterized by ultraviolet (UV) circular dichroism (CD) and 1H-nuclear magnetic resonance (NMR) spectroscopy. The effects of salt concentration (0.1 M and 4 M NaCl), oligomer strand concentration (10-5-10-2M) and temperature (0°-90°C) on the oligomer conformation were investigated. The dimer does not form a duplex under any conditions studied. The tetramer does form a right-handed duplex in 0.1M NaCl even at 3×10-5M strand concentration. In 4M NaCl, however, it does not form any duplex at the same strand concentration, and left-handed duplex formation is observed at 10-fold higher concentration. The hexamer forms a duplex in either salt concentration even at 2×10-5M strand concentration. The melting temperatures of these duplexes were measured by UV and CD methods. The CD-temperature profile in 4M NaCl, which is not sigmoidal when monitored at the λmin of the characteristic negative band, suggests that melting of the high salt duplex is a rather complex process that involves more than two species. The results of 1H-NMR-temperature studies support left-handed duplex formation in a high salt solution.View full abstractDownload PDF (1339K) -
TAMOTSU NIKAIDO, TAICHI OHMOTO, TAKESHI KINOSHITA, USHIO SANKAWA, SANS ...1981 Volume 29 Issue 12 Pages 3586-3592
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclic adenosine monophosphate (AMP) phosphodiesterase inhibitors contained in Forsythia suspensa were identified as lignans, (+)-pinoresinol (Ja) and (+)-pinoresinol-β-D-glucoside (Id), and their structure-activity relationship was investigated. In pinoresinol congeners, the configuration of the two phenyl rings is very important in relation to the activity. When both of the p-hydroxyl groups in matairesinol congeners are substituted by methyl or glucose, the activities are decreased as compared with those of the unsubstituted compounds.View full abstractDownload PDF (700K) -
YOSHISUKE TSUDA, KIMIHIRO YOSHIMOTO, TERUMI NISHIKAWA1981 Volume 29 Issue 12 Pages 3593-3600
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA practical synthetic route to optically active [2R]- and [2S]-1-alkylamino-3-aryloxy-2-propanols (β-blockers) from [2R]-2, 3-O-isopropylideneglyceraldehyde ([R]-1) was developed. Synthesis of the [S]-isomers was carried out as follows. Borohydride reduction of [R]-1 in the presence of excess alkylamine followed by alkoxycarbonylation, acid hydrolysis, and cyclization under K2CO3 catalysis gave [5S]-3-alkyl-5-hydroxymethyl-1, 3-oxazolidin-2-ones, the tosylates of which were coupled with various phenols then hydrolyzed by alkali treatment to give [S]-(-)-β-blockers (e. g., propranolol, carteolol) in satisfactory yields. [R]-, [S]-, and rac-pindolol were synthesized from the corresponding 3-isopropyl-5-(2-methyl-3-nitrophenoxymethyl)-1, 3-oxazolidin-2-one by application of the Leimgruber-Batcho method.View full abstractDownload PDF (969K) -
USHIO SANKAWA, HISAO SHIMADA, KAZUO YAMASAKI1981 Volume 29 Issue 12 Pages 3601-3605
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBiosynthetic incorporation of 2H from [2-13C, 2-2H3]-acetate into 2-hexyl-5-propylresorcinol was investigated in Pseudomonas. The 13C nuclear magnetic resonance spectrum of labelled 2-hexyl-5-propylresorcinol showed 13C-2H signals of expected methylene and methyl carbons in the side chains, but no 2H was found on the aromatic carbons. The main species of methyl groups labelled with 2H were 13C-2H3 and 13C-2H21H. The incorporation experiments unambiguously demonstrate that 2-hexyl-5-propylresorcinol is biosynthesized from two polyketide chains.View full abstractDownload PDF (532K) -
HIROSHI HOSODA, NORIHIRO KOBAYASHI, SHINICHI MIYAIRI, TOSHIO NAMBARA1981 Volume 29 Issue 12 Pages 3606-3610
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe specificity in heterogeneous enzyme immunoassays for cortisol has been investigated. Enzyme labeling of cortisol was accomplished by the N-succinimidyl ester method at an appropriate molar ratio of steroid to enzyme. Three cortisol derivatives possessing different bridges at C-4 were covalently linked to β-galactosidase. The anticortisol antisera used were those elicited in rabbits by immunization with the conjugates of these haptenic derivatives with bovine serum albumin. With the aim of obtaining high sensitivity, enzyme immunoassays were carried out in the bridge heterologous combinations of antiserum and enzyme-labeled cortisol. The specificity of these assay systems was assessed by measuring the amount of cortisol in biological fluids, and by comparison of the results with those of radioimmunoassays. The cross-reactivities were also tested with fifteen kinds of closely related steroids. The assay using the antiserum raised against the 4-(2-carboxyethylthio) cortisol-protein conjugate was found to be relatively specific and applicable to the determination of cortisol in human plasma and urine.View full abstractDownload PDF (648K) -
TOSHIO MIYAZAKI, MOTOHIRO NISHIJIMA1981 Volume 29 Issue 12 Pages 3611-3616
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA water-soluble, antitumor polysaccharide GL-1, [α]20D+26°(c=1, water), M.W. 40000, was isolated from the fruit bodies of Ganoderma lucidum (Rokkakushi, a kind of Reishi). GL-1 consists of glucose, xylose and arabinose in the molar ratio of 18.8 : 1.5 : 1.0. Structural examination was carried out by periodate oxidation, Smith degradation, methylation analysis, partial acid hydrolysis and α-amylase treatment. It is concluded that (1) GL-1 is a branched arabinoxyloglucan, (2) GL-1 contains backbone and side-chains involving D-glucopyranosyl (1→4)-α- and -β-, (1→6)-β- and (1→3)-β-linkages, (3) arabinose is present as a part of the non-reducing terminal residues, and (4) xylose may be present as a part of the side-chain. GL-1 strongly inhibited the growth of Sarcoma 180 solid-type tumor (inhibition ratio, 95.6-98.5%) when injected i. p. (20 mg/kg) for 10 days. Mild acid hydrolysis and α-amylase treatment of GL-1 had no effect on the antitumor activity. These results suggest that the essential structure for the antitumor activity of GL-1 is a branched glucan core (GL-3) involving (1→3)-β-, (1→4)-β-and (1→6)-β-linkages.View full abstractDownload PDF (800K) -
YOSHIO MATSUMOTO, TETSUYA SUGA1981 Volume 29 Issue 12 Pages 3617-3623
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of 3-amino-1, 2, 4-triazole (AT) on the uptake of tritiated p-biphenylmethyl-(dl-tropyl-α-tropinium) bromide (3H-BTTB) into the subcellular fractions of livers of carbon tetrachloride (CCl4)-treated mice were studied. The uptake of 3H-BTTB into the liver of CCl4-treated mice was decreased to 50% of that in the control group. Pretreatment with AT resulted in an effective restoration of the decrease caused by CCl4 treatment up to the AT group's level, though AT itself lowered the uptake of 3H-BTTB to 61% of that of the control group. The subcellular distribution of 3H-BTTB in the liver of CCl4-treated mice was different from that of the control : the ratio of the radioactivity in the lysosomal fraction to that of the supernatant fraction (the L/S ratio) was decreased by CCl4 treatment from 1.85 to 1.66. This decrease was almost completely reversed to the control value by the pretreatment with AT and there was a similar change in the distribution of acid phosphatase. Furthermore, the cross-points of the lysosomes of the liver in mice which had been treated with CCl4, AT and AT-CCl4 were determined by means of cross-partition in aqueous polymer two-phase systems. CCl4 made the surface charge of the lysosomal membrane more acidic, though AT reversed this change. There may be an important relationship between the uptake of BTTB into lysosomes and the characteristics of the lysosomal membranes.View full abstractDownload PDF (698K) -
HIDEO SAWADA, MICHIO SHINODA, HITOMI MARUYAMA, TOSHIHIRO NAKAYAMA1981 Volume 29 Issue 12 Pages 3624-3629
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid phosphatase (orthophosphoric monoester phosphohydrolase, EC 3. 1. 3. 2) isozyme 4 (pI 6.1) has been isolated from human prostate tissue. The enzyme showed a single protein band when examined by polyacrylamide gel disc electrophoresis. The purification coefficient was approximate 3.2 and the recovery of enzyme activity was 0.1% from the supernatant fraction. The molecular weight of the enzyme obtained by gel filtration was 100000, whereas that obtained by polyacrylamide gel electrophoresis in the presence of sodium dodecyl sulfate was 79000. The enzyme was not cross-reactive with acid phosphatase isozyme (pI 5.3) in immunodiffusion. Isozyme 4 had almost the same enzymic properties (Km, Ki, and optimum pH) as isozyme 2, but the specific activity of isozyme 4 was one-fourth of that of the latter.View full abstractDownload PDF (753K) -
SUSUMU SHINAGAWA, MASAHIKO FUJINO, HARUMITSU ISHII, KIYOHISA KAWAI1981 Volume 29 Issue 12 Pages 3630-3638
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThirty tetrapeptide hydrazide analogs of enkephalin, H-Tyr-D-Ala-Gly-Phe-NHN-(R1)-R2 (R1, R2=H, alkyl or acyl), were synthesized. The analgesic activities of these peptides were tested in mice after intravenous or subcutaneous injection, and compared with that of morphine. Among the analogs synthesized, the tetrapeptide acyl-hydrazide analog, H-Tyr-D-Ala-Gly-Phe-NHNH-CO-R (R=lower alkyl), was the most active and showed analgesic activity ten times more potent than that of the tetrapeptide amide analog, H-Tyr-D-Ala-Gly-Phe-NH2 and half as potent as that of morphine. On the basis of these results, structure-activity relations in the hydrazide part of enkephalin analogs of this new type are discussed.View full abstractDownload PDF (911K) -
SUSUMU SHINAGAWA, MASAHIKO FUJINO, HARUMITSU ISHII, KIYOHISA KAWAI1981 Volume 29 Issue 12 Pages 3639-3645
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to study the effect of N-methylation of a potent enkephalin analog, H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH2CH3, on analgesic activity, six new analogs were synthesized in which one or more of amino acid residues and the acyl-hydrazide constituting the tetrapeptide acyl-hydrazide were N-methylated. N-Methylation of both Tyr at position 1 and Phe at position 4 of the analog led to a derivative which was twice as potent as morphine. On the other hand, N-methylation of D-Ala at position 2, Gly at position 3 or NHNH-CO-CH2CH3 at position 5 markedly decreased the analgesic potency. Five analogs with a modified tyrosine residue at position 1 of the tetrapeptide acyl-hydrazide were also synthesized in order to assess the role of the N-terminal Tyr residue in the biological activity.View full abstractDownload PDF (896K) -
SUSUMU SHINAGAWA, MASAHIKO FUJINO, MITSUHIRO WAKIMASU, HARUMITSU ISHII ...1981 Volume 29 Issue 12 Pages 3646-3659
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThirty-five tetrapeptide acyl-hydrazide analogs of enkephalin substituted at position 2 were synthesized. Substitution of D-Ala at position 2 of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-R (R=lower alkyl), by D-Met (O), D-Gln, D-Glu (NH-CH3) or D-Thr enhanced the analgesic potency, but substitution by D-Glu or Ser resulted in an analog with no antinociceptive activity. Among the analogs synthesized, the D-Met (O)-analog was the most potent and H-Tyr-D-Met (O)-Gly-Phe-NHNH-CO-CH2CH3 exhibited analgesic activtiy four times more potent than that of morphine in mice following subcutaneous injection. Structure-activity relations for position 2 of the enkephalin-like tetrapeptide are discussed.View full abstractDownload PDF (1373K) -
MAMORU SUGIURA, KAZUYUKI HIRANO, YUICHI IIIZUMI, JUN MIYAZAKI, KAZUMAS ...1981 Volume 29 Issue 12 Pages 3660-3666
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman alkaline phosphatase was purified from meconium by treatment with cetylpyridinium chloride, followed by diethylaminoethyl (DEAE)-cellulose and CM-cellulose chromatography, Sephadex G-200 gel filtration and DEAE-Sephadex A-50 chromatography. The homogeneity of the purified enzyme was demonstrated by disc electrophoresis and immunological investigation. The molecular weight of the purified meconial alkaline phosphatase was 155000 and the enzyme was composed of two subunits of equal molecular weight. The optimum pH was found to be 10.0 and the enzyme was stable over the pH range of 4-10. The Km value was 2.2mM for p-nitrophenylphosphate as a substrate. The isoelectric point was pH 4.0, and the purified enzyme was inhibited by N-bromosuccinimide (NBS), o-phenanthroline, ethylenediaminetetraacetic acid (EDTA) and L-phenylalanine. Meconial alkaline phosphatase obtained by our method contained 2 g-atoms of zinc/mole of enzyme. The enzymic properties of the purified meconial alkaline phosphatase were compared with those of adult intestinal alkaline phosphatase.View full abstractDownload PDF (944K) -
KENJI MIZOJIRI, ETSUKO YAMAMOTO, YOSHITSUGU NAKAJIMA, HIROSHI OKABE, K ...1981 Volume 29 Issue 12 Pages 3667-3670
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPerisoxal glucuronides were isolated from rabbit urine after repeated subcutaneous administration of dl-perisoxal citrate. Optical rotatory analysis of free bases obtained from the glucuronides indicated that about twice as much d-perisoxal glucuronide as l-isomer was formed. Stereoselective metabolism was observed in rabbit urine after d- or l-perisoxal administration. d-Perisoxal glucuronide was excreted predominantly at doses of 1.8 and 9.0 mg/kg. The excretions of d- and l-isomers of p-hydroxyperisoxal glucuronides were similar at the dose of 9.0 mg/kg, but a larger value was obtained for the l-isomer at the dose of 1.8 mg/kg.View full abstractDownload PDF (500K) -
AKIRA KUSAI, SEIJI TANAKA, SEIGO UEDA1981 Volume 29 Issue 12 Pages 3671-3679
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics and mechanisms of the degradation of 2, 5-diethylenimino-1, 4-benzoquinone (EB) in aqueous solution were investigated as a function of pH (4-11), temperature (20-50°C), buffer concentration (0.01-0.1M) and ionic strength (0.1-0.5) by means of high pressure liquid chromatography. The reaction followed pseudo first-order kinetics. The pH-rate profile showed slopes of -1 at pH below 7.5 and +1 at pH over 7.5. Thus, the degradation of EB is subjected to specific acid-base catalysis. No effect of buffer concentration on the degradation rate of EB was apparent in the range of pH 4-11, though some effect of ionic strength on it was observed below pH 7. The apparent activation energies for the degradation of EB at pH 4 or 5 and pH 10 or 11 were 14 and 19 kcal/mol, respectively. In the range of pH 4-6, EB was degraded to 2, 5-diethanolamino-1, 4-benzoquinone with sequential hydrolytic cleavage of two ethylenimine rings. In the range of pH 10-11, EB was degraded to 2, 5-dihydroxy-1, 4-benzoquinone with sequential substitution of the two ethylenimine rings by hydroxyl ion (radical). In the range of pH 7-9, EB was degraded to 2, 5-diethanolamino-1, 4-benzoquinone, 2, 5-dihydroxy-1, 4-benzoquinone and 2-ethanol-amino-5-hydroxy-1, 4-benzoquinone by the two mechanisms described above.View full abstractDownload PDF (823K) -
HIROMITSU SEKI, TSUYOSHI KAGAMI, TAIZO HAYASHI, NAOYA OKUSA1981 Volume 29 Issue 12 Pages 3680-3687
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the quality control of drug products, it is usually necessary to predict the coloration of parenteral solutions under marketing conditions. This paper presents a new method for the prediction of coloration of parenteral solutions using as examples thiamine hydrochloride injection, reserpine injection, ascorbic acid injection and ATP injection. The time course of decrease of percent transmittance at 430 nm for each parenteral solution was measured spectrophotometrically. When the decreases at elevated temperatures were plotted against time on Weibull probability paper, straight lines were obtained at all temperatures. The temperature dependence of the decrease in each parenteral solution was obtained as a straight regression line on plotting (1/m) In k vs. 1/T. The predicted decreases of percent transmittance for each parenteral solution at 25°C were in good agreement with those observed at 25°C except in the case of reserpine injection. Thus, this method proved to be satisfactory for the quality control of the other three injections and may also be applicable to other injections.View full abstractDownload PDF (680K) -
JYOJI KURITA, HIROKAZU KOJIMA, TAKASHI TSUCHIYA1981 Volume 29 Issue 12 Pages 3688-3695
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermolysis of various 4- and/or 6-methyl-1, 2-diazepines (12a, b and 18a-e), prepared from pyridine and lutidine N-imides (11 and 17a-d) having a methyl group in the 3-position, gave the corresponding 1, 3-diazepines (13 and 19) and the 2-aminopyridine derivatives (14 and 20), whereas 1, 2-diazepines (9a-d) having no methyl group in the 4- or 6-position gave only the parent N-imides (8) and no 1, 3-diazepines. Heating of the 2, 3-diazabicyclo [3. 2. 0] hepta-3, 6-dienes (21a, b) formed from the corresponding 1, 2-diazepines by irradiation also gave the 1, 3-diazepines (13a and 19b).View full abstractDownload PDF (850K) -
JYOJI KURITA, HIROKAZU KOJIMA, MICHIKO ENKAKU, TAKASHI TSUCHIYA1981 Volume 29 Issue 12 Pages 3696-3705
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe thermolysis of 1, 2-diazepines (7a-f and 11) having an electron-donating substituent in the 4- or 6-position resulted in the formation of the 1, 3-diazepines (9 and 12) and 2-aminopyridines (10), whereas 1, 2-diazepines (7g-k) having an electron-withdrawing substituent in the same position gave only 2-aminopyridines (10) and no 1, 3-diazepines. However, the thermolysis of 3-, 5-, or 7-substituted 1, 2-diazepines with either an electron-donating or-withdrawing substituent did not give 1, 3-diazepines. Heating of the bicyclic compounds (8) also gave the corresponding 1, 3-diazepines. Based on these results, we concluded that the presence of an electron-donating substituent is essential for this ring-conversion of 1, 2-diazepines into 1, 3-diazepines. These substituent effects and the reaction mechanism are discussed.View full abstractDownload PDF (1002K) -
TAKUZO HISANO, TOSHIKAZU MATSUOKA, KAZUHIRO TSUTSUMI, KEIJI MURAOKA, M ...1981 Volume 29 Issue 12 Pages 3706-3712
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyridine 1-oxide was subjected to 1, 3-dipolar cycloaddition with phenyl isocyanates having an ortho, meta or para substituent group. The reaction conducted at 90°C in dimethylformamide gave the 2, 3-dihydropyridine-form cycloadduct, although the reaction of pyridine 1-oxide with phenyl isocyanate directly affords 2-anilinopyridine. An increase of the reaction time led to increases in the yields of 2-anilinopyridine and 1-phenyl-carbamoyl-2-phenylimino-1, 2-dihydropyridine, while the yield of the cycloadduct tended to decrease. The reaction at 150°C resulted in an increased yield of 2-anilinopyridine. The reactions of 2-anilinopyridine and 5-methyl-2-anilinopyridine with phenyl isocyanate at room temperature afforded the corresponding 1-phenylcarbamoyl-2-phenylimino-1, 2-dihydropyridines, whereas the reactions of 3-methyl- and 3, 5-dimethyl-2-anilinopyridines with phenyl isocyanate at 90°C afforded 2-(N-phenylcarbamoylanilino) pyridine derivatives.View full abstractDownload PDF (726K) -
JIRO ARITOMI, SHOZO UEDA, HARUKI NISHIMURA1981 Volume 29 Issue 12 Pages 3712-3715
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo ethyl 1, 2-dimethyl-1, 4-dihydroquinoline-3-carboxylate derivatives (I, III) were subjected to the Mannich reaction to give 1-methyl-2-(2-disubstituted aminoethyl) derivatives (II, IV). They are additional examples of the Mannich reaction at the γ-carbon atom of enaminoester compounds.View full abstractDownload PDF (513K) -
TAKUO CHIBA, SUSUMU TSUCHIYA, TETSUZO KATO1981 Volume 29 Issue 12 Pages 3715-3720
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotoreaction of diketene with N-phenylmaleimide (2) and its dimethyl derivative 3 gave rel-(4R, 5S, 6S)- and rel-(4R, 5R, 6R)-2-oxo-1-oxaspiro [3. 3] heptane-5, 6-dicarboximides (4a and 4b) and their dimethyl derivatives 5a and 5b, respectively. Alcoholysis of compounds 4a and 4b with alcoholic hydrogen chloride gave 5-alkoxycarbonyl-4-oxo-N-phenyl-1, 2-pentanedicarboximides 7 and 8, which were transformed to the corresponding 5-alkoxycarbonyl-3-oxoheptanedioates 9 and 10 by further alcoholysis. Compounds 4a and 4b were hydrolyzed with 10% hydrochloric acid to give 3-carboxy-5-oxohexanoic acid (11). Thermolysis of compounds 4a and 4b gave 3-methylenecyclobutane-1, 2-dicarboximide (12).View full abstractDownload PDF (694K) -
YUKIHIRO SHOYAMA, SATOSHI MORIMOTO, ITSUO NISHIOKA1981 Volume 29 Issue 12 Pages 3720-3723
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new neutral propyl cannabinoids, cannabicyclovarin and Δ7-cis-iso-tetrahydrocannabivarin have been isolated from Thai cannabis, "Meao strain."This is the first report of isolation of the latter, which has a novel skeleton, from natural sources.View full abstractDownload PDF (566K) -
MACHIKO MATSUBARA, SYUKO FURUYA, HISATORA KURODA1981 Volume 29 Issue 12 Pages 3723-3726
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSoluble trehalase (EC 3.2.1.28) was isolated and purified from the conidia of Cochliobolus miyabeanus by diethylaminoethyl Sephadex A-50 column chromatography and polyacrylamide gel electrophoresis. The molecular weight of this enzyme was estimated to be 160000 by the gel filtration method. Although the purified trehalase hydrolyzed both trehalose and maltose, this enzyme showed higher activity toward trehalose than maltose (the Km values were 7.3×10-4M for trehalose and 1.5×10-2M for maltose). The optimal pH and temperature for the enzyme reaction were 4.0 and 37°C respectively. The enzyme became unstable at 50°C. This enzyme was competitively inhibited by fructose-6-phosphate and Na-pyruvate.View full abstractDownload PDF (535K) -
MAYURI KUBO, YOSHIAKI KATO, KATSUAKI MORISAKA, YOSHIHIKO INAMORI, KYOS ...1981 Volume 29 Issue 12 Pages 3727-3730
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRacemomycin-A, -C and -B, like racemomycin-D, exhibited insecticidal activity against the adults of Blattella germanica and Musca domestica. These racemomycin compounds, like racemomycin-D, also showed a delayed toxicity on the adult of Blattella germanica. The insecticidal effect of racemomycin-A, -C and -B on both insects was in the order of B>C>A. As the number of β-lysine residues increased, the antibacterial effect increased along with the insecticidal effect. However, racemomycinic A acid, produced by opening of the lactam ring of the streptolidine moiety of racemomycin-A, showed no insecticidal effect. This would suggest an intimate relationship between the streptolidine moiety in the molecule of streptothricin antibiotics and the activity. Citromycin, a streptothricin-like antibiotic, also exhibited an insecticidal effect against the adults of Blattella germanica and Musca domestica, like racemomycin series compounds.View full abstractDownload PDF (467K) -
TADAYORI SHIMIZU, ICHIJI MIFUCHI, TERUO YOKOKURA1981 Volume 29 Issue 12 Pages 3731-3734
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mitogenic activity of whole cells of 18 strains of lactobacilli toward splenocytes from C57BL/6 mice was studied. Although most of the strains showed no mitogenicity, L. fermentum and L. Plantarum were capable of increasing the incorporation of 3H-thymidine (3H-TdR) into splenocytes. Both strains were also able to stimulate the incorporation of 3H-TdR into splenocytes that had been treated with rabbit antithymocyte serum in the presence of complement in order to kill T-lymphocytes, but did not stimulate the incorporation into thymocytes. These results indicate that L. fermentum and L. plantarum cells act on the B-lymphocyte population of splenocytes.View full abstractDownload PDF (532K) -
MASAO NARUSE, KUMIKO YOSHIZAWA, TERUTOSHI KIMURA, SHUMPEI SAKAKIBARA1981 Volume 29 Issue 12 Pages 3734-3737
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDes-Pro2-Bradykinin was synthesized by the classical solution method as a reference compound for a possible contaminant in synthetic bradykinins, and its behavior in various chromatographic analyses was examined. It showed almost the same Rf values as bradykinin under several different conditions in cellulose thin layer chromatography and in paper electrophoresis, but was clearly separable from bradykinin by reversed phase high performance liquid chromatography under specific conditions. Since des-Pro2-bradykinin was found to have a potent bradykinin-potentiating activity, contamination by this material should be carefully avoided in bradykinin synthesis.View full abstractDownload PDF (565K) -
KAZUO TAJIMA, KENJI YAMAMOTO, TAMIO MIZUTANI1981 Volume 29 Issue 12 Pages 3738-3741
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 6-Di-tert-butyl-4-methylene-2, 5-cyclohexadien-1-one (BHT-quinone methide, BHT-QM) was detected in the bile of rats given butylated hydroxytoluene (BHT). The biliary excretion of BHT-QM during 24 h after administration of BHT, 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol (BHT-alcohol), or 2, 6-di-tert-butyl-4-hydroxy-4-methyl-2, 5-cyclohexadien-1-one (4-hydroxy-BHT) was determined by high-performance liquid chromatography. BHT-alcohol gave about 7 times as much BHT-QM as did BHT, but no BHT-QM was detected after administration of 4-hydroxy-BHT. This result suggests that the transformation of BHT to BHT-QM proceeds mainly through BHT-alcohol. Although 1, 2-bis (3, 5-di-tert-butyl-4-hydroxyphenyl) ethane (BHT-dimer) has been reported as a biliary metabolite of BHT in rats, most of the BHT-dimer seems to be formed artificially by dimerization of BHT-QM during the isolation process.View full abstractDownload PDF (530K) -
NAOMI YAGI, ISAO AGATA, TAEKO KAWAMURA, YOHKO TANAKA, MIEKO SAKAMOTO, ...1981 Volume 29 Issue 12 Pages 3741-3747
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPlasma concentration profiles of sulfadimethoxine, sulfamethoxazole and their biotransformed products (N4-acetate and N1-glucuronide) in dogs were determined and their pharmacokinetic parameters were calculated by using a two-compartment open model. The apparent partition coefficients between chloroform and phosphate buffer were also determined. Decline in plasma levels of sulfadimethoxine and sulfamethoxazole was considerably accelerated by N4-acetylation and N1-glucuronidation. The elimination of sulfadimethoxine-N1-glucuronide from plasma was more rapid than that of sulfadimethoxine-N4-acetate, and a similar tendency was observed for sulfamethoxazole and its biotransformed products. N4-Acetylation or N1-glucuronidation of sulfadimethoxine and sulfamethoxazole decreased the lipid solubilities markedly in comparison with those of original sulfonamides.View full abstractDownload PDF (668K) -
TOSHIHIKO OKAMOTO, KOICHI SHUDO, SOSHIRO TAKAHASHI, EMIKO KAWACHI, YO ...1981 Volume 29 Issue 12 Pages 3748-3750
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCytokinins initiate or promote cell division and cell differentiation of plants. N-(4-Pyridyl)-N'-phenylureas with an electronegative substituent (s) at positions 2 and 6 of the pyridine ring are the strongest cytokinins so far known. Structure-activity relationships between urea- and purine-cytokinins were discussed.View full abstractDownload PDF (415K) -
FUMIYA KUROSAKI, SOSHIRO TAKAHASHI, KOICHI SHUDO, TOSHIHIKO OKAMOTO, Y ...1981 Volume 29 Issue 12 Pages 3751-3753
Published: December 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructural and biological correlation between two classes of cytokinins, purine- and urea-cytokinins, were discussed. The biological response in the presence of competitive antagonists of cytokinins suggested that benzyladenine and N-(4-pyridyl)-N'-phenylurea have a common active site for the growth of tobacco callus.View full abstractDownload PDF (439K)